The first catalytic asymmetric total synthesis of ent-hyperforin

被引：34

作者：

Shimizu, Yohei ^{[1
]}

Shi, Shi-Liang ^{[1
]}

Usuda, Hiroyuki ^{[1
]}

Kanai, Motomu ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

基金：

日本学术振兴会;

关键词：

HYPERICUM-PERFORATUM-L; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; GARSUBELLIN-A; ABSOLUTE-CONFIGURATION; BRIDGEHEAD LITHIATION; CLUSIANONE; OXIDATION; OLEFINS; (+/-)-CLUSIANONE; DERIVATIVES;

D O I：

10.1016/j.tet.2010.05.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric total synthesis of ent-hyperforin was described here in detail. Keys to the success were a catalytic asymmetric Diels-Alder reaction, a stereoselective Clasien rearrangement, an intramolecular aldol cyclization, and a vinylogous Pummerer rearrangement. Along with the successful synthetic route, several attempted approaches toward the construction of bicyclo[3.3.1] core and the C2 oxidation were discussed. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6569 / 6584

页数：16

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