A chemoenzymatic synthesis of the linear triquinane (-)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer

被引：56

作者：

Banwell, MG ^{[1
]}

Edwards, AJ ^{[1
]}

Harfoot, GJ ^{[1
]}

Jolliffe, KA ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia

来源：

TETRAHEDRON | 2004年 / 60卷 / 03期

关键词：

chemoenzymatic; hirsutene; sesquiterpene; triquinane; oxadi-pi-methane; enantiodivergence; cycloaddition; cis-1,2-dihydrocatechol;

D O I：

10.1016/j.tet.2003.10.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiomerically pure cis-1,2-dihydrocatechol, which is readily obtained via a toluene dioxygenase-mediated dihydroxylation of toluene in a whole-cell biotransformation process, has been converted over 17 steps into the linear triquinane (-)-hirsutene. Since the enantiomer of the starting material is also available this work constitutes a formal total synthesis of the naturally occurring (+)-form of hirsutene. Furthermore, minor modifications of the route used here offer the possibility of accessing (+)-hirsutene from the original starting material. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：535 / 547

页数：13