A simple and efficient chemoenzymatic total synthesis of the naturally occurring insect pheromones, (4R)-dodecanolide and (4R)-octanolide is described.
ChalierP, CrouzetJ. (1998) Enantio differentiation of four γ-lactones produced by Penicillium roqueforti. Chirality, 10, 786–790.
8.
FlathRA, BlackDR, GuadagniDG, Mc. FaddenWH, SchultzTH. (1967) Identification and organoleptic evaluation of compounds in delicious apple essence. Journal of Agricultural and Food Chemistry, 15, 29–35.
9.
TangCS, JenningsWG. (1968) Lactonic compounds of apricot. Journal of Agricultural and Food Chemistry, 16, 252–254.
10.
JurriensG, OleleJM. (1965) Determination of hydro xy-acid triglycerides and lactones in butter. Journal of the American Oil Chemists’ Society, 42, 857–861.
11.
YadavJS, ManiyanPP. (1993) A convenient chiral synthesis of 4-alkyl-γ-butanolides. Synthetic Communications, 23, 2731–2741
12.
UziR, SilversteinRM, SmithLR. (1978) Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration. Tetrahedron, 34, 1449–1452.
13.
MoriK. (1992) In The Total Synthesis of Natural Products, Vol. 9. SimonJA. (Ed). John Wiley & Sons, New York, 216–273
14.
BoniniC, FedericiC, RossiL, RighiG. (1995) C-l reactivity of 2,3-epoxy alcohols via oxirane opening with metal halides: Application and synthesis of naturally occurring 2,3-octanediol, muricatacin, 3-octanol, and 4-dodecanolide. Journal of Organic Chemistry, 60, 4803–4812
15.
HislopJ, HuntMB, FielderS, RowanD. (2004) Synthesis of deuterated γ-lactones for use in stable isotope dilution assays. Journal of Agricultural and Food Chemistry, 52, 7075–7083
16.
CereV, MazziniC, PaolucciC, PollicinoS, FavaA. (1993) Dihyro- and tetrahydrofuran building blocks from l,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R, 7R) endo-(-)- and (1S, 5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide. Journal of Organic Chemistry, 58, 4567–4571
17.
KakeyaH, SakaiN, SugaiT, OhtaH. (1991) Preparation of optically active α-hydroxy acid derivatives by microbial hydrolysis of cyanohydrins and its application to the total synthesis of (R)-4-dodeeanolide. Agricultural and Biological Chemistry, 55, 1877–1881
18.
FedericiC, RighiG, RossiL, BoniniC, ChiummientoL, FunicelloM. (1994) Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols. Tetrahedron Letters, 35, 797–800
19.
GansäuerA, FanC, KellerF, KeilJ. (2007) Titanocene-catalyzed regiodivergent epoxide openings. Journal of American Chemical Society, 129, 3484–3485.
20.
MidlandMM. (1975) Preparation of monolithium acetylide in tetrahydrofuran. Reaction with aldehydes and ketones. Journal of Organic Chemistry, 40, 2250–2252
For lipase-catalyzed resolution of racemic propargylic alcohols, see: (a) OhtaniT, KikuchiK, KamezawaM, HamataniH, TachibanaH, TotaniT, NaoshimaY. (1996) Chemoenzymatic synthesis of (+)-(4E’,15E)-docosa-4,15-dien-l-yn-3-ol, a component of the marine sponge Cribrochalina vasculum. Journal of the Chemical Society, Perkin Transactions1, 961–1969
23.
OhtaniT, NakatsukasaH, KamezawaM, TachibanaH, NaoshimaY. (1998) Enantioselectivity of Candida antarctica lipase for some synthetic substrates including aliphatic secondary alcohols. Journal of Molecular Catalysis B; Enzymatic, 4, 53–60
24.
MorishitaK, KamezawaM, OhtaniT, TachibanaH, KawaseM, KishimotoM, NaoshimaY. (1999) Chemoenzymatic synthesis of (+)-docosa-4,15-dien-l-yn-3-ol, a component of the marine sponge Cribrochalina vasculum, and confirmation of the structure and absolute configuration of the acetylenic alcohol, by lipase-catalysed bio-transformations. Journal of the Chemical Society, Perkin Transactions1, 513–518.
25.
RaminelliC, ComassetoJV, AndradeLH, PortoALM. (2004) Kinetic resolution of propargylic and allylic alcohols by Candida antarctica lipase (Novozyme 435). Kinetic resolution of propargylic and allylic alcohols by Candida antarctica lipase (Novozyme 435). Tetrahedron; Asymmetry, 15, 3117–3122
26.
YadavJS, DeshpandePK, SharmaGVM. (1990) An effective practical method for the synthesis of chiral propargyl alcohols. Tetrahedron, 46, 7033–7046.
27.
YadavJS, SreenivasM, ReddyAS, ReddyBVS. (2010) A practical total synthesis of (+)-spirolaxine methyl ether. Journal of Organic Chemistry, 75, 8307–8310
28.
NakataM, OhashiJ, OhsawaK, NishimuraT, KinoshitaM, TatsutaK. (1993) Synthetic studies of venturicidins. Synthesis of the C1-C14 segment of venturicidins. Bulletin of the Chemical Society of Japan, 66, 3464–3474.