Enantioselective synthesis of natural (-)-tochuinyl acetate, (-)-dihydrotochuinyl acetate and (+)-β-cuparenone using both enantiomers of the same building block

被引：18

作者：

Acherar, S ^{[1
]}

Audran, G ^{[1
]}

Cecchin, F ^{[1
]}

Monti, H ^{[1
]}

机构：

[1] Fac Sci & Tech St Jerome, UMR 6180 Chirotechnol Catalyse & Biocatalyse, Lab Reaqct Organ Select, F-13397 Marseille 20, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 28期

关键词：

total synthesis; configuration determination; enantioselectivity; cuparane family; lipases;

D O I：

10.1016/j.tet.2004.05.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective synthesis of tochuinyl acetate and dihydrotochuinyl acetate, two natural marine products isolated from Tochuina tetraquetra and Gersemia rubiformis, has been achieved starting from an enantiopure building block. The key feature of the present synthesis is complete control of two vicinal quaternary stereogenic centers present in the natural products and elucidation of their absolute stereochemistry, which was previously unknown. Furthermore, starting from the enantiomer of the same building block, the applied methodology provided a new approach towards natural (R)-(+)-beta-cuparenone. (C) 2004 Published by Elsevier Ltd.

引用

页码：5907 / 5912

页数：6

共 23 条

[1] Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene [J].