Total synthesis of insect pheromones (R)-4-dodecanolide and (S)-5-hexadecanolide

被引：35

作者：

Sabitha, Gowravaram ^{[1
]}

Reddy, E. Venkata ^{[1
]}

Yadagiri, K. ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2006年 / 19期

关键词：

pheromone; natural product; dodecanolide; hexadecanolide; chiral lactones;

D O I：

10.1055/s-2006-950212

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of naturally occurring insect pheromones, (R)-4-dodecanolide and (S)-5-hexadecanolide has been achieved in a simple and efficient way with high yields.

引用

页码：3270 / 3274

页数：5

共 35 条

[1] MICROBIOLOGICAL TRANSFORMATIONS .13. A DIRECT SYNTHESIS OF BOTH S-ENANTIOMER AND R-ENANTIOMER OF 5-HEXADECANOLIDE VIA AN ENANTIOSELECTIVE MICROBIOLOGICAL BAEYER-VILLIGER REACTION [J].

ALPHAND, V ;

ARCHELAS, A ;

FURSTOSS, R .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :347-350

[2]

BIN S, 2005, CHINESE J CHEM, V23, P1228

[3] SYNTHESIS OF BOTH ENANTIOMERS OF GAMMA-SUBSTITUTED ALPHA, BETA-UNSATURATED GAMMA-LACTONES [J].

BLOCH, R ;

GILBERT, L .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4603-4605

[4] C-1 REACTIVITY OF 2,3-EPOXY ALCOHOLS VIA OXIRANE OPENING WITH METAL-HALIDES - APPLICATIONS AND SYNTHESIS OF NATURALLY-OCCURRING 2,3-OCTANEDIOL, MURICATACIN, 3-OCTANOL, AND 4-DODECANOLIDE [J].

BONINI, C ;

FEDERICI, C ;

ROSSI, L ;

RIGHI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4803-4812

[5]

Chalier P, 1998, CHIRALITY, V10, P786, DOI 10.1002/(SICI)1520-636X(1998)10:9<786::AID-CHIR2>3.0.CO

[6]

2-8

[7]

Davies-Coleman M T, 1989, Fortschr Chem Org Naturst, V55, P1

[8]

FERNANDEZ AM, 1995, SYNLETT, P431

[9] IDENTIFICATION AND ORGANOLEPTIC EVALUATION OF COMPOUNDS IN DELICIOUS APPLE ESSENCE [J].

FLATH, RA ;

BLACK, DR ;

GUADAGNI, DG ;

MCFADDEN, WH ;

SCHULTZ, TH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1967, 15 (01) :29-&

[10] LIPASE-CATALYZED KINETIC RESOLUTION OF METHYL 4-HYDROXY-5-TETRADECYNOATE AND ITS APPLICATION TO A FACILE SYNTHESIS OF JAPANESE-BEETLE PHEROMONE [J].

FUKUSAKI, E ;

SENDA, S ;

NAKAZONO, Y ;

OMATA, T .

TETRAHEDRON, 1991, 47 (32) :6223-6230

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