Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction

被引：17
|
作者：
Drège, E
Morgant, G
Desmäle, D
机构：
[1] Univ Paris 11, Fac Pharm, CNRS, Unite Chim Organ Associee, F-92290 Chatenay Malabry, France
[2] Fac Pharm Chatenay Malabry, Lab Cristallog Bioinorgan, F-92296 Chatenay Malabry, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 42期
关键词：
terpenes and terpenoids; Michael reactions; Heck reactions; ring transformation; diazo compounds;
D O I：
10.1016/j.tetlet.2005.07.157
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7263 / 7266
页数：4
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