A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

被引：58

作者：

Fischer, Joshua ^{[1
]}

Savage, G. Paul ^{[2
]}

Coster, Mark J. ^{[1
]}

机构：

[1] Griffith Univ, Eskitis Inst Cell & Mol Therapies, Nathan, Qld 4111, Australia

[2] CSIRO Mat Sci & Engn, Clayton, Vic 3169, Australia

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

基金：

澳大利亚研究理事会;

关键词：

CELL-SUSPENSION CULTURES; C-H INSERTION; SALVIA-MILTIORRHIZA; ALPHA; BETA-UNSATURATED ESTERS; CARBONYLATIVE ANNULATION; LITHOSPERMUM-RUDERALE; ASYMMETRIC-SYNTHESIS; CONJUGATE REDUCTION; PALLADIUM-THIOUREA; DERIVATIVES;

D O I：

10.1021/ol201130h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.

引用

页码：3376 / 3379

页数：4

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