Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

被引：32

作者：

Ohtsuki, Keiko

Matsuo, Kazumasa

Yoshikawa, Takashi

Moriya, Chihiro

Tomita-Yokotani, Kaori

Shishido, Kozo

Shindo, Mitsuru

机构：

[1] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Tsukuba, Ibaraki 3058572, Japan

[3] Univ Tokushima, Grad Sch Pharmaceut Sci, Tsukuba, Ibaraki 3058572, Japan

[4] Univ Tsukuba, Grad Sch Life & Environm Sci, Tsukuba, Ibaraki 3058572, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 06期

关键词：

D O I：

10.1021/ol8001333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. They-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph(3)P=CMe(CO(2)R).

引用

页码：1247 / 1250

页数：4

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