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

被引：57
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
收藏
页码：3376 / 3379
页数：4
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