Total synthesis of the mushroom metabolite (+)-calopin

被引：15

作者：

Ebel, H ^{[1
]}

Knör, S ^{[1
]}

Steglich, W ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

TETRAHEDRON | 2003年 / 59卷 / 01期

关键词：

natural product synthesis; calopin; lactones; asymmetric synthesis; ene reaction;

D O I：

10.1016/S0040-4020(02)01451-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of (+)-calopin (1a) was achieved employing a highly stereoselective ene reaction between 8-phenylmenthyl glyoxylate (3) and the beta,beta-dimethylstyrene 4c. Transesterification of the resulting homoallylic alcohol 5c, followed by allylic oxidation and hydrogenation yielded the delta-lactone 13 which was deprotected to the natural product 1a. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：123 / 129

页数：7

共 15 条

[1]

Ebel H, 2002, EUR J ORG CHEM, V2002, P2905, DOI 10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO

[2]

2-3

[3]

EBEL H, 2002, THESIS U MUNICH

[4] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].