Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose

被引：42

作者：

Amano, S ^{[1
]}

Ogawa, N ^{[1
]}

Ohtsuka, M ^{[1
]}

Chida, N ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(99)00004-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral synthesis of the immunosuppressive sesquiterpene; FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd-catalyzed Stilie coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2205 / 2224

页数：20

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