Stereocontrolled synthesis of (±)-methyl 3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate, a major metabolite of Caribbean sponge, Plakortis halichondrioides, using reactions of alkylidenecarbenes in one pot

被引：22

作者：

Akiyama, M ^{[1
]}

Isoda, Y ^{[1
]}

Nishimoto, M ^{[1
]}

Kobayashi, A ^{[1
]}

Togawa, D ^{[1
]}

Hirao, N ^{[1
]}

Kuboki, A ^{[1
]}

Ohira, S ^{[1
]}

机构：

[1] Okayama Univ Sci, Fac Sci, Dept Biol Chem, Okayama 7000005, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 44期

关键词：

(+/-)-methyl (2Z,6R*,8R*,9E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate; plakortone; alkylidenecarbene; 1,2 hydride shift; 1,5 C-H insertion;

D O I：

10.1016/j.tetlet.2005.09.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-Methyl (2Z,6R*,8R*,9E)-3,6-epoxy-4,6,8-triethy1-2,4,9-dodecatrienoate, a major metabolite of the Caribbean sponge, was synthesized in a stereocontrolled manner from gamma-caprolactone. The key step was one-pot generation of alkylidenecarbenes at two sites followed by 1,2 hydride shift and intramolecular 1,5 C-H insertion. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7483 / 7485

页数：3

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