Total Synthesis of Hyperforin

被引：75

作者：

Ting, Chi P. ^{[1
]}

Maimone, Thomas J. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 33期

关键词：

POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; STEREOSELECTIVE TOTAL-SYNTHESIS; ALKYLATIVE DEAROMATIZATION-ANNULATION; PHLOROGLUCIN NATURAL-PRODUCTS; ASYMMETRIC TOTAL-SYNTHESIS; BIOMIMETIC TOTAL-SYNTHESIS; GARSUBELLIN-A; CONJUGATE ADDITION; GRIGNARD-REAGENTS; FORMAL SYNTHESIS;

D O I：

10.1021/jacs.5b06939

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 10-step total synthesis of the polycyclic polyprenylated acylphloroglucinol (PPAP) natural product hyperforin from 2-methylcydopent-2-en-l-one is reported. This route was enabled by a diketene annulation reaction and an oxidative ring expansion strategy designed to complement the presumed biosynthesis of this complex meroterpene. The described work enables the preparation of a highly substituted bicyclo[3.3.1]nonane-1,3,5-trione motif in only six steps and thus serves as a platform for the construction of easily synthesized, highly diverse PPAPs modifiable at every position.

引用

页码：10516 / 10519

页数：4

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