Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples which would pave the way for further biological studies.
WohlfarthC, EfferthT., (2009) Natural products as promising drug candidates for the treatment of hepatitis B and C. Acta Pharmacologica Sinica, 30, 25–30.
5.
WardropDJ, WaidyarachchiSL. (2010) Synthesis and biological activity of naturally occurring α-glucosidase inhibitors. Natural Product Reports, 27, 1431–1468.
6.
GrutersRA, NeefjesJJ, TersmetteM, GoedeREY, TulpA, HuismanHG, MiedemaF, PloeghHL. (1987) Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase. Nature, 330, 74–77.
CompainP, MartinOR. (2003) Design, synthesis and biological evaluation of iminosugar-based glycosyltransferase inhibitors. Current Topics in Medicinal Chemistry, 3, 541–560.
9.
ZouW. (2005) C-Glycosides and aza-C-glycosides as potential glycosidase and glycosyltransferase inhibitors. Current Topics in Medicinal Chemistry, 5, 1363–1391.
FedorovA, ShiW, KicskaG, FedorovE, TylerPC, FurneauxRH, HansonJC, GainsfordGJ, LareseJZ, SchrammVL, AlmoSC. (2001) Transition state structure of purine nucleoside phosphorylase and principles of atomic motion in enzymatic catalysis. Biochemistry, 40, 853–860.
12.
YagiM, KounoT, AoyagiY, MuraiH., (1976) The structure of moraoline, a piperidine alkaloid from Morus species. Nippon Nougei Kagaku Kaish, 50, 571–572.
13.
ZhuYP, YamakiK, YoshihashiT, KameyamaMO, LiXT, ChengYQ, MoriY, LiLT. (2010) Purification and identification of 1-deoxynojirimycin (DNJ) in okra fermented by Bacillus subtilis B2 from Chinese traditional food (Meitaoza). Journal of Agricultural and Food Chemistry, 58, 4097–4103.
14.
WelterA, JadotJ, DardenneG, MarlierM, CasimirJ., (1976) 2,5-Dihydroxymethyl 3,4-dihydroxypyrrolidine dans les feuilles de Derris elliptica. Phytochemistry, 15, 747–749.
15.
MolyneuxRJ, BensonM, WongRY, TropeaJE, ElbeinAD. (1988) Australine, a novel pyrrolizidine alkaloid glucosidase inhibitor from Castanospermum australe. Journal of Natural Products, 51, 1198–1206.
16.
NashRJ, FellowsLE, DringJV, FleetGWJ, DeromeAE, HamorTA, ScofieldAM, WatkinDJ. (1988) Isolation from Alexa leiopetala and X-ray crystal structure of alexine, (1R,2R,3R,7S,8S)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine [(2R,3R,4R,5S,6S)-2-hydroxymethyl-1-azabicyclo[3.3.0]octan-3,4,6-triol], a unique pyrrolizidine alkaloid. Tetrahedron Letters, 29, 2487–2490.
17.
KatoA, AdachiI, MiyauchiM, IkedaK, KomaeT, KizuH, KamedaY, WatsonAA, NashRJ, WormaldMR, FleetGWJ, AsanoN., (1999) Polyhydroxylated pyrrolidine and pyrrolizidine alkaloids from Hyacinthoides non-scripta and Scilla campanulata. Carbohydrate Research, 316, 95–103
18.
AsanoN, KuroiH, IkedaK, KizuH, KamedaY, KatoA, AdachiI, WatsonAA, NashRJ, FleetGWJ. (2000) New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: structural determination and biological activity. Tetrahedron: Asymmetry, 11, 1–8.
19.
HohenschutzLD, BellEA, JewessPJ, LeworthyDP, PryceRJ, ArnoldE, ClardyJ., (1981) Castanospermine, a 1,6,7,8-tetrahydroxyoctahydroindolizine alkaloid, from seeds of Castanospermum australe. Phytochemistry, 20, 811–814.
20.
AsanoN, KatoA, OsekiK, KizuH, MatsuiK., (1995) Calystegins of Physalis alkekengi var. francheti (Solanaceae): structure determination and their glycosidase inhibitory activities. European Journal of Biochemistry, 229, 369–376.
21.
DembitskyVM. (2005) Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides. Lipids, 40, 1081–1105.
22.
MeloEB, GomesAS, CarvalhoI., (2006) α-and β-Glucosidase inhibitors: chemical structure and biological activity. Tetrahedron, 62, 10277–10302.
23.
InouyeS, TsuruokaT, NiidaT., (1966) Structure of nojirimycin, sugar antibiotic with nitrogen in the ring. Journal of Antibiotics, 19, 288–292.
24.
IshidaN, KumagaiK, NiidaT, TsuruokaT, YumotoH., (1967) Nojirimycin, a new antibiotic. II. Isolation, characterization, and biological activity. Journal of Antibiotics, 20, 66–71.
25.
InouyeS, TsuruokaT, ItoT, NiidaT., (1968) Structure and synthesis of nojirimycin. Tetrahedron, 24, 2125–2144.
26.
SomsakL, NagyV, HadadyZ, DocsaT, GergelyP., (2003) Glucose analog inhibitors of glycogen phosphorylases as potential antidiabetic agents: recent developments. Current Pharmaceutical Design, 9, 1177–1189.
27.
GreimelP, SpreitzJ, StutzAE, WrodniggTM. (2003) Iminosugars and relatives as antiviral and potential anti-infective agents. Current Topics in Medicinal Chemistry, 3, 513–523.
28.
NishimuraY. (2003) gem-Diamine 1-N-iminosugars and related iminosugars, candidate of therapeutic agents for tumor metastasis. Current Topics in Medicinal Chemistry, 3, 575–591.
JacobGS. (1995) Glycosylation inhibitors in biology and medicine. Current Opinion in Structural Biology, 5, 605–611.
31.
SegravesNL, CrewsP., (2005) A Madagascar sponge Batzella sp. as a source of alkylated iminosugars. Journal of Natural Products, 68, 118–121.
32.
SakaiR, KamiyaH., (2006) 1-Deoxynojirimycin derivatives from the marine sponge Lendenfeldia chondrodes. The Journal of Antibiotics, 59, 507–511.
33.
ScudderPR, DwekRA, RademacherTW, JacobGS. (1991) Preparation of phosphorylated polyhydroxylated pyrrolidines and piperidines as glycosidase inhibitor prodrugs. European Patent Application, EP 413674 A2 19910220.
34.
JacobGS. (1993) Aminosugar inhibitors as anti-HIV agents. Frontiers in Biomedicine and Biotechnology, 1, 74–86.
35.
SaludesJP, LievensSC, MolinskiTF. (2007) Occurrence of the γ-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol and related iminopentitols in marine sponges. Journal of Natural Products, 70, 436–438.
36.
YodaH, KitayamaH, KatagiriH, TakabeK., (1993) Synthesis of natural lentiginosine employing a cyclic imide with C2-symmetry derived from L-tartaric acid. Tetrahedron: Asymmetry, 4, 1455–1456.
37.
YodaH, NakajimaT, TakabeK., (1997) Stereocontrolled synthesis of a trihydroxylated indolizidine alkaloid, 1-deoxycastanospermine. Synlett, 1997, 911–912.
38.
YodaH, KawauchiM, TakabeK., (1998) Novel asymmetric synthesis of an indolizidine alkaloid, (+)-lentiginosine employing highly stereoselective hydrogenation of α-hydroxypyrrolidine. Synlett, 1998, 137–138.
39.
YodaH, KatohH, TakabeK., (2000) Asymmetric total synthesis of natural pyrrolizidine alkaloid, (+)-alexine. Tetrahedron Letters, 41, 7661–7665.
40.
YodaH, KatohH, UjiharaY, TakabeK., (2001) SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (-)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine. Tetrahedron Letters, 42, 2509–2512.
41.
TakahashiM, MaeharaT, SengokuT, FujitaN, TakabeK, YodaH., (2008) New asymmetric strategy for the total synthesis of naturally occurring (+)-alexine and (-)-7-epi-alexine. Tetrahedron, 64, 5254–5261.
42.
SengokuT, SatohY, OshimaM, TakahashiM, YodaH., (2008) First asymmetric synthesis of pyrrolizidine alkaloids, (+)-hyacinthacine B1 and (+)-B2. Tetrahedron, 64, 8052–8058.
43.
SengokuT, SatohY, TakahashiM, YodaH., (2009) Total synthesis of the proposed structures of hyacinthacines C2, C3, and their C5-epimers. Tetrahedron Letters, 50, 4937–4940.
44.
WierzejskaJ, OhshimaM, InuzukaT, SengokuT, TakahashiT, YodaH., (2011) Total synthesis and absolute stereochemistry of (+)-batzellaside B and its C8-epimer, a new class of piperidine alkaloids from the sponge Batzella sp. Tetrahedron Letters, 52, 1173–1175.
45.
WierzejskaJ, MotogoeS, MakinoY, SengokuT, TakahashiM, YodaH., (2012) A new approach toward the total synthesis of (+)-batzellaside B. Beilstein Journal of Organic Chemistry, 8, 1831–1838.
46.
TejimaS, FletcherHGJr. (1963) Syntheses with partially benzylated sugars. II. The anomeric 1-O-benzoyl-L-arabinopyranoses and 1-O-benzoyl-L-arabinofuranoses and their tendencies to undergo acyl migration. The Journal of Organic Chemistry, 28, 2999–3004.
LayL, NicotraF, PaganiniA, PangrazioC, PanzaL., (1993) A new procedure for the synthesis of azasugars. Tetrahedron Letters, 34, 4555–4558.
49.
HashimotoM, TerashimaS., (1994) A stereoselective synthesis of a novel model compound of carzinophilin carrying the C6-C13 unit with correct stereochemistry. Chemistry Letters, 23, 1001–1002.
50.
YodaH, YamazakiH, KawauchiM, TakabeK., (1995) An efficient asymmetric functionalization to highly substituted pyrrolidines. Tetrahedron: Asymmetry, 6, 2669–2672.
51.
YodaH, NakajimaT, TakabeK., (1996) Total synthesis of natural (-)-codonopsinine employing stereoselective reduction of quaternary α-hydroxypyrrolidine. Tetrahedron Letters, 37, 5531–5534.
52.
YodaH, OguchiT, TakabeK., (1997) Novel asymmetric synthesis of penaresidin B as a potent actomyosin ATPase activator. Tetrahedron Letters, 38, 3283–3284.
53.
YodaH, UemuraT, TakabeK., (2003) Novel and practical asymmetric synthesis of an azetidine alkaloid, penaresidin B. Tetrahedron Letters, 44, 977–979.
54.
LucheJL. (1978) Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones. Journal of the American Chemical Society, 100, 2226–2227.
55.
GemalAL, LucheJL. (1981) Lanthanoids in organic synthesis. 6. Reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects. Journal of the American Chemical Society, 103, 5454–5459.
56.
BartonDHR, McCombieSW. (1975) A new method for the deoxygenation of secondary alcohols. Journal of the Chemical Society, Perkin Transactions1, 1574–1585.
57.
BartonDHR, JaszberenyiJC. (1989) Improved methods for the radical deoxygenation of secondary alcohols. Tetrahedron Letters, 30, 2619–2622.
58.
CrichD, QuinteroL., (1989) Radical chemistry associated with the thiocarbonyl group. Chemical Reviews, 89, 1413–1432.
59.
TsujiJ, ShimizuI, MinamiI., (1984) Regioselective synthesis of 1-olefins by palladium-catalyzed hydrogenolysis of terminal allylic compounds with ammonium formate. Chemistry Letters, 13, 1017–1020.
60.
JakoI, UiberP, MannA, TaddeiM, WermuthCG. (1990) Diastereoselectivity in conjugate addition of alkylcuprates to vinylogous ester of N,O-diprotected serinal. Tetrahedron Letters, 31, 1011–1014.
61.
JakoI, UiberP, MannA, WermuthCG, BoulangerT, NorbergB, EvrardG, DurantF., (1991) Stereoselective synthesis of 3-alkylated glutamic acids: application to the synthesis of secokainic acid. The Journal of Organic Chemistry, 56, 5729–5733.
62.
IkotaN. (1992) Synthesis of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone from (S)-pyroglutaminol. Chemical and Pharmaceutical Bulletin, 40, 1925–1927.
63.
OliveiraDJ, CoelhoF., (2000) Highly diastereoselective alkylation of a pyroglutamate derivative with an electrophile obtained from indole. synthesis of a potential intermediate for the preparation of the natural sweetener (-)-monatin. Synthetic Communications, 30, 2143–2159.
64.
YokoyamaM, IkenogamiT, TogoH., (2000) Stereoselective synthesis of C-4′-aminouridines (uracil C-4-amino-D-ribonucleosides). Journal of the Chemical Society, Perkin Transactions1, 2067–2071.
65.
BunchL, NorrbyPO, FrydenvargK, Krogsgaard-LarsenP, MadsenU., (2001) Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol. Organic Letters, 3, 433–435.
66.
AcevedoCM, KogutEF, LiptonMA. (2001) Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid. Tetrahedron, 57, 6353–6359.
67.
FriemanBA, BockCW, BhatKL. (2001) A facile entry to bicyclic systems from L-glutamic acid. Heterocycles, 55, 2099–2018.
68.
OliveiraDJ, CoelhoF., (2001) Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of monatin. Tetrahedron Letters, 42, 6793–6796.
69.
BrennemanJB, MachauerR, MartinSF. (2004) Enantioselective synthesis of (+)-anatoxin-A via enyne metathesis. Tetrahedron, 60, 7301–7314.
70.
QiuXL, QingFL. (2005) Synthesis of 3′-deoxy-3′-difluoromethyl azanucleosides from trans-4-hydroxy-l-proline. The Journal of Organic Chemistry, 70, 3826–3837.
71.
FiauxH, KuntzDA, HoffmanD, JanzerRC, Gerber-LemaireS, RoseDR, Juillerat-JeanneretL. (2008) Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: optimizing the fit to the active site. Bioorganic and Medicinal Chemistry, 16, 7337–7346.
72.
LarsenAM, VenskutonytėR, ValadésEA, NielsenB, PickeringDS, BunchL. (2011) Discovery of a new class of ionotropic glutamate receptor antagonists by the rational design of (2S,3R)-3-(3-carboxyphenyl)-pyrrolidine-2-carboxylic acid. ACS Chemical Neuroscience, 2, 107–114.
73.
RasmussenJL, StorgaarM, PickeringDS, BunchL., (2011) Rational design, synthesis and pharmacological evaluation of the (2R)- and (2S)-stereoisomers of 3-(2-carboxypyrrolidinyl)-2-methyl acetic acid as ligands for the ionotropic glutamate receptors. ChemMedChem, 6, 498–504.
74.
FlynnDL, ZelleRE, GriecoPA. (1983) A mild two-step method for the hydrolysis of lactams and secondary amides. The Journal of Organic Chemistry, 48, 2424–2426.
75.
YodaH, ShiraiT, KatagiriT, TakabeK, KimataK, HosoyaK., (1990) Stereoselective Michael addition of organometallic reagents to α,β-unsaturated ester containing oxazolidine ring. Chemistry Letters, 19, 2037–2038.
76.
SpangenbergT, SchoenfelderA, BreitB, MannA., (2010) 1,2-Diastereoselective C-C bond-forming reactions for the synthesis of chiral β-branched α-amino acids. European Journal of Organic Chemistry, 6005–6018.
77.
CoreyEJ, VenkateswarluA., (1972) Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. Journal of the American Chemical Society, 94, 6190–6191.
78.
KlugeAF, UntchKG, FriedJH. (1972) Synthesis of prostaglandin models and prostaglandins by conjugate addition of a functionalized organocopper reagent. Journal of the American Chemical Society, 94, 7827–7832.
79.
VanReenenV, KellyRC, ChaDY. (1976) An improved catalytic OsO4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant. Tetrahedron Letters, 17, 1973–1976.
80.
SharplessKB, AkashiK., (1976) Osmium catalyzed vicinal hydroxylation of olefins by tert-butyl hydroperoxide under alkaline conditions. Journal of the American Chemical Society, 94, 6190–6191.
81.
HentgesSG, SharplessKB. (1980) Asymmetric induction in the reaction of osmium tetroxide with olefins. Journal of the American Chemical Society, 102, 4263–4265.
82.
JacobsenEN, MarkoI, MungallWS, SchroederG, SharplessKB. (1988) Asymmetric dihydroxylation via ligand-accelerated catalysis. Journal of the American Chemical Society, 110, 1968–1970.
83.
SharplessKB, AmbergW, BennaniYL, CrispinoGA, HartungJ, JeongKS, KwongHL, MorikawaK, WangSM. (1992) The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement. The Journal of Organic Chemistry, 57, 2768–2771.
NicolaouKC, YueEW, GrecaSL, NadinA, YangZ, LerescheJE, TsuriT, NaniwaY, RiccardisFD. (1995) Synthesis of zaragozic acid A/squalestatin S1. Chemistry - A European Journal, 1, 467–494.
86.
PabbaJ, RempelBP, WithersSG, VasellaA., (2006) Synthesis of glycaro-1,5-lactams and tetrahydrotetrazolopyridine-5-carboxylates: inhibitors of β-D-glucuronidase and α-L-iduronidase. Helvetica Chimica Acta, 89, 635–666.
87.
ReetzMT, KesselerK., (1985) Chelation- and non-chelation-controlled additions to 2-O-benzyl-3-O-(tert-butyldimethylsilyl)glyceraldehyde. The Journal of Organic Chemistry, 50, 5434–5436.
88.
UchidaM, TabusaF, KomatsuM, MoritaS, KanbeT, NakagawaK., (1985) Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid and related compounds. Chemical and Pharmaceutical Bulletin, 33, 3775–3786.
89.
PlattnerJJ, GlessRD, RapoportH. (1972) Synthesis of some DE and CDE ring analogs of camptothecin. Journal of the American Chemical Society, 94, 8613–8615.
90.
MastCA, EißlerS, StončiusA, StammlerHG, NeumannB, SewaldN. (2005) Efficient and versatile stereoselective synthesis of cryptophycins. Chemistry - A European Journal, 11, 4667–4677.
91.
Shi-JunW, Hong-WangZ, Zhu-JunY. (2002) Synthesis of a fully protected (2S,3R)-N-(1′,1′-dimethyl-2′- propenyl)-3-hydroxytryptophan from tryptophan. Tetrahedron Letters, 43, 5291–5294.
92.
ChiesaMV, ManzoniL, ScolasticoC., (1996) A practical way to 2,5-disubstituted pyrrolidine derivatives. Synlett, 1996, 441–443.
ArtaleE, BanfiG, BelvisiL, ColomboL, ColomboM, ManzoniL, ScolasticoC., (2003) Synthesis of substituted conformationally constrained 6,5- and 7,5-fused bicyclic lactams as dipeptide mimics. Tetrahedron, 59, 6241–6250.
95.
EschPM, HiemstraH, KlaverWJ, SpeckampWN. (1987) An N-acyliminium route to the 8-azabicyclo[3.2.1]octane (tropane) and the 9-azabicyclo[4.2.1]nonane ring system synthesis of (±)-anatoxin-A. Heterocycles, 26, 75–79.
96.
SiskoJ, WeinrebSM. (1991) Construction of the tricyclic core of the marine alkaloid sarain A. The Journal of Organic Chemistry, 56, 3210–3211.
97.
SiskoJ, HenryJP, WeinrebSM. (1993) Development of a strategy for synthesis of the unusual marine alkaloid sarain A. The Journal of Organic Chemistry, 58, 4945–4951.
98.
MentinkG, MaarseveenJH, HiemstraH., (2002) Allenylmethylsilanes as nucleophiles in N-acyliminium ion chemistry. Organic Letters, 4, 3497–3500.
99.
GeCS, HourcadeS, FerdenziA, ChiaroniA, MonsS, DelpechB, MarazanoC., (2006) A biogenetically based strategy towards the polycyclic core skeleton of sarain A. European Journal of Organic Chemistry, 4106–4114.
100.
OthmanRB, AffaniR, TranchantMJ, AntoniottiS, DallaV, DuñachE. (2009) N-Acyliminium ion chemistry: highly efficient and versatile carbon-carbon bond formation by nucleophilic substitution of hydroxy groups catalyzed by Sn(NTf2)4. Angewandte Chemie International Edition, 49, 776–780.
101.
WangY, ZhuS, MaD., (2011) Organocatalytic approach to polysubstituted piperidines and tetrahydropyrans. Organic Letters, 13, 1602–1605.
102.
DaleJA, MosherHS. (1968) Nuclear magnetic resonance nonequivalence of diastereomeric esters of α-substituted phenylacetic acids for the determination of stereochemical purity. Journal of the American Chemical Society, 90, 3732–3738.
103.
DaleJA, MosherHS. (1973) Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. Journal of the American Chemical Society, 95, 512–519.
104.
SullivanGR, DaleJA, MosherHS. (1973) Correlation of configuration and 19F chemical shifts of α-methoxy-α-trifluoromethylphenyl acetate derivatives. The Journal of Organic Chemistry, 38, 2143–2147.
105.
OhtaniI, KusumiT, KashmanY, KakisawaH., (1991) High-field FT NMR application of Mosher's method. The absolute configuration of marine terpenoids. Journal of the American Chemical Society, 113, 4092–4096.
106.
SecoJM, QuinoaE, RigueraR., (2004) The assignment of absolute configuration by NMR. Chemical Reviews, 104, 17–117.
107.
GrubbsRH, ChangS., (1998) Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron, 54, 4413–4450.
108.
ChatterjeeAK, ChoiTL, SandersDP, GrubbsRH. (2003) A general model for selectivity in olefin cross metathesis. Journal of the American Chemical Society, 125, 11360–11370.
109.
NicolaouKC, BulgerPG, SarlahD., (2005) Metathesis reactions in total synthesis. Angewandte Chemie International Edition, 44, 4490–4257.
110.
SajikiH, HattoriK, HirotaK., (1998) The formation of a novel Pd/C-ethylenediamine complex catalyst: chemoselective hydrogenation without deprotection of the O-benzyl and N-Cbz groups. The Journal of Organic Chemistry, 63, 7990–7992.
111.
GriffithWP, LeySV, WhitcombeGP, WhiteAD. (1987) Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols. Journal of the Chemical Society, Chemical Communications, 1625–1627.
112.
Very recently an analogous example for the synthesis of unnatural batzellasides has appeared in the literature: OkakiT, FujimuraR, SekiguchiM, ZhouD, SugimotoK, MinatoD, MatsuyaY, KatoA, AdachiI, TezukaY, SaporitoRA, ToyookaN., (2013) Stereoselective total synthesis of (–)-batzellasides A, B, and C. European Journal of Organic Chemistry, 2841–2848.
