Synlett 2006(16): 2655-2657  
DOI: 10.1055/s-2006-951480
LETTER
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of 4α,5α,10β-Trihydroxycadinane and Its C 4-Isomer: ­Structural Revision of a Natural Sesquiterpenoid

Lijing Fang, Fuqiang Bi, Chen Zhang, Guojun Zheng, Yulin Li*
State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
Fax: +86(931)8912283; e-Mail: liyl@lzu.edu.cn;
Further Information

Publication History

Received 3 July 2006
Publication Date:
22 September 2006 (online)

Zoom Image

Abstract

An efficient approach to cadinane sesquiterpenes starting from (R)-carvone, employing a ring closing metathesis (RCM) reaction and a modified allylic diazene rearrangement as key steps, is described. The first asymmetric total syntheses of 4α,5α,10β-trihydroxycadinane (1) and natural 4β,5α,10β-trihydroxycadinane (2) were accomplished and the structure of natural product A was revised to 2.