Stereocontrolled Total Synthesis of Tetrodotoxin from myo -Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
Free accessResearch articleFirst published online May, 2015
Stereocontrolled Total Synthesis of Tetrodotoxin from myo -Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative, tetrodotoxin, containing eight asymmetric carbons and different types of branched-chains, from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives), but also for other highly complex multi-functionalized cyclitols containing branched-chains.
TsudaK, IkumaS, KawamuraM, TachikawaK, SakaiK, TamuraC, AmakasuO. (1964) Tetrodotoxin. VII. On the structures of tetrodotoxin and its derivatives. Chemical & Pharmaceutical Bulletin, 12, 1357-1374.
WoodwardRB. (1964) Structure of tetrodotoxin. Pure and Applied Chemistry, 9, 49-74;
5.
WoodwardRBGougoutasJZ. (1964) Structure of tetrodotoxin. Journal of the American Chemical Society, 86, 5030-5030.
6.
MosherHSFuhrmanFABuchwaldHDFischerHG. (1964) Tarichatoxin- tetodotoxin: A potent neurotoxin. Science, 144, 1100-1110.
7.
NarahashiT, MooreJWScottWR. (1964) Tetrodotoxin blockage of sodium conductance increase in lobster giant axons. Journal of General Physiology, 47, 965-974.
8.
NarahashiT. (1974) Chemicals as tools in the study of excitable membranes. Physiological Reviews, 54, 813-889;
9.
HuchoF. (1995) Toxins as tools in neurochemistry. Angewandte Chemie, International Edition in English, 34, 39-50;
10.
BalernaM, LombetA, ChicheporticheR, RomeyG, LazdunskiM. (1981) Synthesis and properties of new photoactivable derivatives of tetrodotoxin. Biochimica et Biophysica Acta, Biomembranes, 644, 219-225;
11.
BontempsJ, CantineauR, GrandfilsC, LeprinceP, DandrifosseG, SchoffenielsE. (1984) High-yield synthesis of a [3H]ethylenediamine ditetrodotoxin derivative. Analytical Biochemistry, 139, 149-157;
12.
WuBQYangL, KaoCYLevinsonSRYotsu-YamashitaM, YasumotoT. (1996) 11-Oxo-tetrodotoxin and a specifically labeled 3H-tetrodotoxin. Toxicon, 34, 407-416.
13.
YasumotoT, YasumuraD, YotsuM, MichishitaT, EndoA, KotakiY. (1986) Bacterial production of tetrodotoxin and anhydrotetrodotoxin. Agricultural and Biological Chemistry, 50, 793-795;
14.
NoguchiT, JeonJ-K, ArakawaO, SugitaH, DeguchiY.ShidaY, HashimotoK. (1986) Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrio sp. isolated from the intestines of a xanthid crab, Atergatis floridus. Journal of Biochemistry, 99, 311-314.
15.
YasumotoT. (1989) Analytical methods of toxins from marine source and their applications. Kagaku to seibutsu (in Japanese), 27, 401-406;
16.
Yotsu-YamashitoM, YamagishiY, YasumotoT. (1995) 5,6,11-Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus. Tetrahedron Letters, 36, 9329-9332;
17.
ShimizuY, KobayashiM. (1983) Apparent lack of tetrodotoxin biosynthesis in captured Taricha torosa and Taricha granulosa. Chemical & Pharmaceutical Bulletin, 31, 3625-3631;
18.
ShimizuY. (1986) Chemistry and biochemistry of saxitoxin analogs and tetrodotoxin. Annals of the New York Academy of Sciences, 479, 24-31.
19.
For examples of TTX analogs, 5,6,11-trideoxyTTX:
20.
Yotsu-YamashitaM, YamagishiY, YasumotoT. (1995) 5,6,11-Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus. Tetrahedron Letters, 36, 9329-9332;
21.
NakagawaT, JangJ, Yotsu-YamashitaM. (2006) Hydrophilic interaction liquid chromatography-electrospray ionization mass spectrometry of tetrodotoxin and its analogs. Analytical Biochemistry, 352, 142-144;
22.
UmezawaT, HayashiT, SakaiH, TeramotoH, YoshikawaT, IzumidaM, TamataniY, HiroseT, OhfuneY, ShinadaT. (2006) Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer. Organic Letters, 8, 4971–4974. 1-Hydroxy-5,11-dideoxyTTX:
23.
KotakiY, ShimizuY. (1993) 1-Hydroxy-5,11-dideoxytetrodotoxin, the first N-hydroxy and ring-deoxy derivative of tetrodotoxin found in the newt Taricha granulosa. Journal of the American Chemical Society, 115, 827–830. 4-epiTTX:
24.
YasumotoT, MichishitaT. (1985) Fluorometric determination of tetrodotoxin by high-performance liquid chromatography. Agricultural and Biological Chemistry, 49, 3077–3088. 6-epi TTX, 11-deoxyTTX:
25.
YasumotoT, YotsuM, MurataM, NaokiH. (1988) New tetrodotoxin analogs from the newt Cynops ensicauda. Journal of the American Chemical Society, 110, 2344–2345. 8,11-dideoxyTTX:
26.
NishikawaT, UrabeD, YoshidaK, IwabuchiT, AsaiM, IsobeM. (2004) Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, an unnatural analogue of puffer fish toxin. Chemistry-European Journal, 10, 452-462;
27.
NishikawaT, UrabeD, YoshidaK, IwabuchiT, AsaiM, IsobeM. (2002) Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin. Organic Letters, 4, 2679–2682. 11-oxoTTX:
28.
KhoraSSYasumotoT. (1989) Isolation of 11-oxotetrodotoxin from the puffer fish Arothron nigropunctatus. Tetrahedron Letters, 30, 4393–4394. 11-norTTX-6(R)-ol:
29.
EndoA, KhoraSSMurataM, YasumotoT. (1988) Isolation of 11-nortetrodotoxin-6(R)-ol and other tetrodotoxin derivatives from the puffer Fugu niphobles. Tetrahedron Letters, 29, 4127–4128. 11-norTTX-6(S)-ol:
30.
YotsuM, HayashiY, KhoraSSSatoS, YasumotoT. (1992) Isolation and structural assignment of 11-nortetrodotoxin-6(S)-ol from the puffer Arothron nigropunctatus. Bioscience, Biotechnology, and Biochemistry, 56, 370–371. 5,11-dideoxyTTX:
AdachiM, ImazuT, IsobeM, NishikawaT. (2013) An improved synthesis of (-)-5,11-dideoxytetrodotoxin. Journal of Organic Chemistry, 78, 1699–1705. Several TTX analogs:
33.
Yotsu-YamashitaM. (2001) Chemistry of puffer fish toxin. Journal of Toxicology, Toxin Reviews, 20, 50-66;
34.
Yotsu-YamashitaM, GotoA, NakagawaT. (2005) Identification of 4-S-cysteinyltetrodotoxin from the liver of the puffer fish, Fugu pardalis, and formation of thiol adducts of tetrodotoxin from 4,9-anhydrotetrodotoxin. Chemical Resaerch Toxicology, 18, 865-871.
35.
KodamaM, OgataT, SatoS. (1985) External secretion of tetrodotoxin from puffer fishes stimulated by electric shock. Marine Biology (Berlin, Germany), 87, 199-202;
36.
MatsumuraK. (1995) Tetrodotoxin as a pheromone. Nature (London), 378, 563-564;
37.
SaitoT, NoguchiT, HaradaT, MurataO, HashimotoK. (1985) Tetrodotoxin as a biological defense agent for puffers. Nippon Suisan Gakkaishi (in Japanese), 51, 1175-1180.
38.
KaoCYLovinsonS. (1986) Structure-activity relations of tetrodotoxin, saxitoxin, and analogs. Annals of the New York Academy of Sciences, 479, 52-67;
NoyaB, ParedesMDOzoresL, AlonsoR. (2000) 5-Exo radical cyclization onto 3-alkoxyketimino-1,6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin Journal of Organic Chemistry, 65, 5960-5968;
41.
BurgeyCSVollerthunR, Fraser-ReidB. (1996) Armed/disarmed effects and adamantyl expansion of some caged tricyclic acetals en route to tetrodotoxin. Journal of Organic Chemistry, 61, 1609-1618;
42.
NachmanRJHonelM, WilliamsTMHalaskaRCMosherHS. (1986) Methyl 3-formyl-2,3-O-isopropylidene-D-erythrofuranoside (D-apiose aldal) and derivatives. Journal of Organic Chemistry, 51, 4802-4806;
43.
KeanaJfw, BlandJSBoylePJErionM, HartlingR, HusmanJRRomanRB. (1983) Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. 8. A series of highly functionalized pyrimidinones. Journal of Organic Chemistry, 48, 3621-3626;
44.
KeanaJfw, BlandJSBoylePJErionM, HartlingR, HusmanJRRomanRB. (1983) Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. 9. Hydroquinazolines possessing the carbon skeleton of tetrodotoxin. Journal of Organic Chemistry, 48, 3627-3631;
45.
ItohT, WatanabeM, FukuyamaT. (2002) Synthetic approach to tetrodotoxin. Synlett, 1323–1325;
46.
OhtaniY, ShinadaT, OhfuneY. (2003) Stereoselective construction of a contiguous tetraol system in tetrodotoxin by means of repetitive operations involving epoxidation and ring-opening reactions of allyl sulfone. Synlett, 619–622;
47.
Fernandez-GonzalezM, AlonsoR. (2006) Formation of five- and six-membered carbocycles with nitrogenated tetra-substituted carbons by radical addition-carbocyclization of alkynyl ketoxime ethers. Journal of Organic Chemistry, 71, 6767-6775;
48.
TaberDFStorckPH. (2003) Synthesis of (-)-tetrodotoxin: Preparation of an advanced cyclohexenone intermediate. Journal of Organic Chemistry, 68, 7768-7771.
49.
KishiY, ArataniM, FukuyamaM, NakatsuboF, GotoT, InoueS, TaninoH, SugiuraS, KakoiH. (1972) Synthetic studies on tetrodotoxin and related compounds. III. Stereospecific synthesis of an equivalent of acetylated tetrodamine. Journal of the American Chemical Society, 94, 9217-9219;
50.
KishiY, FukuyamaT, ArataniM, NakatsuboF, GotoT, InoueS, TaninoH, SugiuraS, KakoiH. (1972) Synthetic studies on tetrodotoxin and related compounds. IV. Stereospecific total syntheses of DL-tetrodotoxin Journal of the American Chemical Society, 94, 9219-9221.
51.
OhyabuN, NishikawaT, IsobeM. (2003) First asymmetric total synthesis of tetrodotoxin. Journal of the American Chemical Society, 125, 8798-8805;
52.
NishikawaT, UrabeD, IsobeM. (2004) Natural product synthesis: An efficient total synthesis of optically active tetrodotoxin. Angewandte Chemie, International Edition, 43, 4782-4785;
53.
UrabeD, NishikawaT, IsobeM. (2006) An efficient total synthesis of optically active tetrodotoxin from levoglucosenone. Chemistry-An Asian Journal, 1–2, 125–135;
54.
HinmamA, Du BoisJ. (2003) A stereoselective synthesis of (-)-tetrodotoxin. Journal of the American Chemical Society, 125, 11510-11511;
55.
KoertU. (2004) Syntheses of tetrodotoxin. Angewandte Chemie International Edition, 43, 5572-5576;
56.
IsobeM, OhyabuN, NishikawaT. (2007) The first asymmetric total synthesis of tetrodotoxin, a puffer fish toxin. Journal of Synthetic Organic Chemistry, Japan. (Yuki Gosei Kagaku Kyokaishi), 65, 492-501;
57.
NishikawaT, KoideY, AdachiM, IsobeM. (2010) Synthesis of an advanced intermediate bearing two hydroxy groups for (-)-tetrodotoxin and its analogs. Bulletin of the Chemical Society of Japan, 83, 66-68;
58.
SatakeY, NishikawaT, HiramatsuT, ArakiH, IsobeM. (2010) Scalable synthesis of a new dihydroxylated intermediate for tetrodotoxin and its analogues. Synthesis, 1992–1998;
59.
NishikawaT, IsobeM. (2013) Synthesis of tetrodotoxin, a classic but still fascinating natural product. The Chemical Record, 13, 286-302.
60.
SatoK, AkaiS, SugitaN, OhsawaT, KogureT, ShojiH, YoshimuraJ. (2005) Novel and stereocontrolled synthesis of (±)-tetrodotoxin from myo-inositol. Journal of Organic Chemistry, 70, 7496-7504;
61.
SatoK, AkaiS, ShojiH, SugitaN, YoshidaS, NagaiY, SuzukiK, NakamuraY, KajiharaY, FunabashiM, YoshimuraJ. (2008) Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose. Journal of Organic Chemistry, 73, 1234-1242;
62.
AkaiS, SekiH, SugitaN, KogureT, NishizawaN, SuzukiK, NakamuraY, KajiharaY, YoshimuraJ, SatoK. (2010) Total synthesis of (-)-tetrodotoxin from D-glucose: a new route to multi-functionalized cyclitol employing the Ferrier(II) reaction toward (-)-tetrodotoxin. Bulletin of the Chemical Society of Japan, 83, 279-287.
63.
NohedaP. (2007) Synthesis of tetrodotoxin, its analogs and intermediates thereof. EP 1785427 A1 20070516.
64.
ChauJ, CiufoliniMA. (2011) The chemical synthesis of tetrodotoxin: An ongoing quest. Marine Drugs, 9, 2046-2074.
65.
HanessianS. (1983) The concept of “chiral templates” and ‘chirons’ –A visual dialogue with the target. In Total Synthesis of Natural Products: The “Chiron” Approach. Organic Chemistry Series. Vol. 3, BaldwinJE. (Ed.), Pergamon Press, Oxford, UK, 21-26.
66.
YoshimuraJ, KobayashiK, SatoK, FunabashiM. (1972) Configuration of branched-chain derivatives of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose. Bulletin of the Chemical Society of Japan, 45, 1806-1812;
67.
YoshimuraJ, MikamiK, SatoK, ShinC. (1976) Branched-chain sugars. VIII. On the configuration of branched-chain sugars from methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose. Bulletin of the Chemical Society of Japan, 49, 1686-1689;
68.
YoshimuraJ, SatoK. (1978) Branched-chain sugars. XII. The stereoselectivities in the reaction of methyl 4,6-O-benzylidene-α- and -β-D-hexopyranosid-3-uloses with diazomethane. Bulletin of the Chemical Society of Japan, 51, 2116-2121;
69.
YoshimuraJ, SatoK, FunabashiM. (1979) Branched-chain sugars. XVII. Stereoselectivity in the oxidation of several methyl 4,6-O-benzylidene-2-C- or –3-C-methylene-α- and -β-D-hexopyranosides with m-chloroperbenzoic acid. Bulletin of the Chemical Society of Japan, 52, 2630-2634;
70.
YoshimuraJ, SatoK. (1979) Branched-chain sugars. Part XIII. Stereoselectivities in the reaction of methyl 4,6-O-benzylidene-α- and -β-D-hexopyranosid-2-uloses with diazomethane. Carbohydrate Research, 73, 75-84;
71.
MatsuzawaM, SatoK, YasumoriT, YoshimuraJ. (1981) Branched-chain sugars. XXIII. Stereoselectivities in the addition of nucleophiles to several 4-uloses. Bulletin of the Chemical Society of Japan, 54, 3505-3509;
72.
YoshimuraJ, SatoK. (1983) Branched-chain sugars, part XXXIII. Complementary stereoselectivity in the reactions of hexopyranosid-4-uloses with methylmagnesium iodide and methyl lithium. Carbohydrate Research, 123, 341-346.
73.
SatoK, SuzukiK, UedaM, KatayamaM, KajiharaY. (1991) A novel reagent for the synthesis of branched-chain functionalized sugars. Dichloromethyl lithium. Chemistry Letters, 1469–1472;
74.
SatoK, SuzukiK, UedaM, KajiharaY, HoriH. (1997) Useful intermediates, 3-C-dichloromethyl furanose derivatives, for the synthesis of branched-chain functionalized sugars. Bulletin of the Chemical Society of Japan, 70, 225-230.
For reviews of the Henry reaction, see: LuzzioFA. (2001) The Henry reaction: recent examples. Tetrahedron, 57, 915-945.
77.
For reviews of the Ferrier (II) reaction, see:
78.
FerrierRJMiddletonS. (1993) The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes. Chemical Reviews, 93, 2779-2831;
79.
TakahashiH. (2002) Synthetic studies on sugar-related bioactive substances based on the ring transformation. Yakugaku Zasshi, 122, 755-771;
80.
BenderSLBudhuRJ. (1991) Biomimetic synthesis of enantiomerically pure D-myo-inositol derivatives. Journal of the American Chemical Society, 113, 9883-9885.
81.
FunabashiM, WakaiH, SatoK, YoshimuraJ. (1980) Branched-chain sugars. XV. Synthesis of 1L-(1,2,3′,4,5/3,6)-3-hydroxumethyl-4,5-O-isopropylidene-3,3′-O-methylene-6-nitro-2,3,4,5-tetrahydroxy-cyclohexanaldehyde dimethylacetal-potential key compound for total synthesis of optically active tetrodotoxin. Journal of Chemical Society, Perkin I, 14–19;
82.
SatoK, KajiharaY, NakamuraY, YoshimuraJ. (1991) Synthesis of functionalized cyclohexanecarbaldehyde derivative. A potential key compound for total synthesis of optically active tetrodotoxin. Chemistry Letters1559–1562
83.
SatoK, SakumaS, NakamuraY, KajiharaY, YoshimuraJ. (1991) Synthesis of methyl-branched 2,3,4,5-tetrahydroxycyclohexanone derivatives via 6-deoxyhex-5-enopyranosides. Chemistry Letters, 17-20.
84.
SatoK, BokuraM, MoriyamaH, IgarashiT. (1994) Total synthesis of a novel β-glucosidase inhibitor, cyclophellitol starting from D-glucose. Chemistry Letters, 37-40.
85.
SatoK, BokuraM, TaniguchiM. (1994) Syntheses of optically active 2,3,6-tri-O-benzyl-D-myo-inositol, laminitol, and mytilitol from D-glucose. Bulletin of the Chemical Society of Japan, 67, 1633-1640.
86.
All intermediates were racemic unless otherwise noted.
87.
LeeHWKishiY. (1985) Synthesis of mono- and unsymmetrical bis-orthoesters of scyllo-inositol. Journal of Organic Chemistry, 50, 4402-4404;
88.
BillingtonDCBakerR. (1987) Synthesis of myo-inositol 1,3,4,5-tetraphosphate and myo-inositol 1,3-bisphosphate. Journal of the Chemical Society, Chemical Communications, 1011–1013;
89.
BaudinG, GlazerBISwaminathanKSVasellaA. (1988) A synthesis of 1D- and 1L-myo-inositol 1,3,4,5-tetraphosphate. Helvetica Chimica Acta, 71, 1367-1378.
90.
InchTDLewisGJ. (1972) Synthesis and degradation of benzyl 4,6-O-benzylidene-2,3-dideoxy-3-C-ethyl-2-C-hydroxymethyl-α-D-glucopyr anoside and -mannopyranoside. Carbohydrate Research, 22, 91-101.
91.
ChanTHChangE, VinokurEM. (1970) The synthesis of olefins and ketones from carbonyl compounds and carbanions alpha to silicon. Tetrahedron Letters, 14, 1137-1140.
92.
DessDBMartinJC. (1991) A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. Journal of the American Chemical Society, 113, 7277-7287;
93.
DessDBMartinJC (1983) Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. Journal of Organic Chemistry, 48, 4155-4156.
SatoK, KajiharaY, NakamuraY, YoshimuraJ. (1991) Synthesis of the functionalized cyclohexanecarbaldehyde derivative. A potential key compound for total synthesis of optically active tetrodotoxin. Chemistry Letters, 1559-1562.
96.
KimKSQianL. (1993) Synthesis of 4,4-difluoro-L-arginine. Tetrahedron Letters, 34, 7195-7196;
97.
BergeronRJMcManisJS. (1987) Total synthesis of (±)-15-deoxyspergualin. Journal of Organic Chemistry, 52, 1700-1703.
98.
A sample of natural (-)-tetrodotoxin was obtained from Sankyo Co. Ltd. (Tokyo, Japan).
99.
LucaLDGiacomelliG, PorchedduA. (1975) Chemistry of epoxides. XXXI. Acid-catalyzed reactions of epoxides with dimethyl sulfoxide. Journal of Organic Chemistry, 40, 2764-2769.
100.
SzarekWAJewellJSSzczerekI, JonesJkn. (1969) Addition of pseudohalogens to unsaturated carbohydrates. III. Synthesis of 3-deoxy-3-C-nitromethyl-D-allose, a branched-chain nitro sugar. Canadian Journal of Chemistry, 47, 4473-4476;
101.
RosenthalA, SprinzlM. (1969) Branched-chain sugar nucleosides. IV. 9-(3-Deoxy-3-C-hydroxymethyl-β (and α)-D-allofuranosyl and ribofuranosyl) adenine. Canadian Journal of Chemistry, 47, 4477-4481;
102.
KarthaKpr. (1986) Iodine, a novel catalyst in carbohydrate reactions. I. O-Isopropylidenation of carbohydrates. Tetrahedron Letters, 27, 3415-3416;
103.
YoshimuraJ, SatoK, HashimotoH. (1977) Synthesis of uloses by the oxidation with dimethyl sulfoxide-trifluoroacetic anhydride. Chemistry Letters, 1327–1330;
104.
KinoshitaM, TaniguchiM, MoriokaM, TakamiH, MizusawaY. (1988) Synthetic studies of amphotericin B. III. An enantiospecific synthesis of the C(1)-C(19) segment of the amphotericin B aglycon. Bulletin of the Chemical Society of Japan, 61, 2147-2156.
105.
The IUPAC name of compound 44 is 1-L-(1,2,3′,4,5/3,6)-3-hydroxymethyl-3,3′-di-O-benzyl-6-nitro-2,3,4,5-tetrahydroxy-cyclohexancarbaldehyde diphenyldithioacetal.
106.
OteroJMBarciaJCSalasCOThomasP, EstévezJCEstévezRJ. (2012) Studies on the Michael addition of naphthoquinones to sugar nitro olefins: first synthesis of polyhydroxylated hexahydro-11H-benzo[a]carbazole-5,6-diones and hexahydro-11bH-benzo[b]carbazole-6,11-diones. Tetrahedron, 68, 1612-1622;
107.
BaerH, RankW. (1965) Reactions of nitro sugars. III. Instability of 6-deoxy-6-nitroaldohexoses at intermediate pH values. Canadian Journal of Chemistry, 43, 3462-3465;
108.
YoshimuraJ, FunabashiM, ShinC.-G. (1980) Syntheses of a few branched-chain aminocyclitol antibiotics In Aminocyclitol Antibiotics. ACS Symposium Series, Vol. 125, RinehartKL Jr., SuamiT. (Eds). American Chemical Society, Washington DC 75-93.
109.
Review of Nef reaction: (a) BalliniR, PetriniM. (2004) Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction). Tetrahedron, 60, 1017-1047;
110.
McMurryJEMeltonJ, PadgettH. (1974) New method for converting nitro compounds, into carbonyls. Ozonolysis of nitronates. Journal of Organic Chemistry, 39, 259-260.
111.
Review: von StadenLFGravestockD, AgerDJ. (2002) New developments in the Peterson olefination reaction. Chemical Society Reviews, 31, 195-200.
112.
FunabashiM, SatoH, YoshimuraJ. (1976) Branched-chain sugars. V. Stereoselective synthesis of 3-C- and 5-C-methyl-D-glucoses, and 5-C-methyl-L-idose derivatives. Bulletin of the Chemical Society of Japan, 49, 788–790.
