DIASTEREOSELECTIVE DESULFURIZATION OF 5,6-DIHYDRO-1,4-DITHIINS - SYNTHESIS OF MUSCALURE FROM MUSCA-DOMESTICA L

被引：23

作者：

CAPUTO, R ^{[1
]}

PALUMBO, G ^{[1
]}

PEDATELLA, S ^{[1
]}

机构：

[1] UNIV NAPLES,DIPARTIMENTO CHIM ORGAN & BIOL,I-80134 NAPLES,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)85249-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure is reported for the chemo- and stereo-selective sulfur removal from 5,6-dihydro-1,4-dithiins which completes the pathway to synthesize cis configurated olefins from carbonyl compounds. A four step synthesis of (Z)-9-tricosene (muscalure) with the dithiin moiety serving as the penultimate olefin precursor is also reported as an example of the proposed synthetic strategy.

引用

页码：7265 / 7268

页数：4

共 12 条

[1]

AUGUSTINE RL, 1965, CATALYTIC HYDROGENAT, P26

[2] NEW DESULFURIZATIONS BY NICKEL-CONTAINING COMPLEX REDUCING AGENTS [J].

BECKER, S ;

FORT, Y ;

CAUBERE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6194-6198

[3]

CAPUTO R, 1991, SYNTHESIS-STUTTGART, P223

[4]

CAPUTO R, 1994, IN PRESS SYNTH COMMU

[5] SEX ATTRACTANT PHEROMONE OF HOUSE FLY - ISOLATION, IDENTIFICATION AND SYNTHESIS [J].

CARLSON, DA ;

MAYER, MS ;

SILHACEK, DL ;

JAMES, JD ;

BEROZA, M ;

BIERL, BA .

SCIENCE, 1971, 174 (4004) :76-&

[6]

FERRERI C, 1991, COMPREHENSIVE ORGANI, V1, P141

[7]

LASZLO P, 1964, B SOC CHIM FR, P87

[8] THE SYNTHESIS OF LONG-CHAIN ALIPHATIC ACIDS FROM ACETYLENIC COMPOUNDS .3. THE SYNTHESIS OF LINOLEIC ACID [J].

RAPHAEL, RA ;

SONDHEIMER, F .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG) :2100-2103

[9] VERSATILE SYNTHESIS OF 5,6-DIHYDRO-1,4-DITHIEPINS AND THEIR SYNTHETIC APPLICATIONS [J].

SAIGO, K ;

HASHIMOTO, Y ;

FANG, L ;

HASEGAWA, M .

HETEROCYCLES, 1989, 29 (11) :2079-2082

[10] A NEW SELECTIVE DESULFURIZATION METHOD [J].

TRUCE, WE ;

PERRY, FM .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1316-&

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