Methyl (3R,5R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether

被引：4

作者：

Mineeva, I. V. ^{[1
]}

机构：

[1] Belarusian State Univ, Minsk 220030, BELARUS

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 49卷 / 06期

关键词：

RU-BINAP COMPLEX; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DELTA-LACTONE; CONVERGENT SYNTHESIS; CHIRAL SULFOXIDES; HIGHLY POTENT; STRATEGY; ACID; SYSTEM;

D O I：

10.1134/S1070428013060067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient asymmetric synthesis of (5S,7R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3R,5R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.

引用

页码：838 / 842

页数：5

共 68 条

[1] STUDIES ON THE BIOSYNTHESIS OF ALIPHATIC LACTONES IN SPOROBOLOMYCES-ODORUS - CONVERSION OF (S)-13-HYDROXY-(Z,E)-9,11-OCTADECADIENOIC ACID AND (R,S)-13-HYDROXY-(Z,E)-9,11-OCTADECADIENOIC ACID INTO OPTICALLY PURE (R)-DELTA-DECALACTONE [J].