Divergent Synthesis of Pyrone Diterpenes via Radical Cross Coupling

被引：72

作者：

Merchant, Rohan R. ^{[1
]}

Oberg, Kevin M. ^{[1
,3
]}

Lin, Yutong ^{[1
]}

Novak, Alexander J. E. ^{[1
]}

Felding, Jakob ^{[2
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

[2] LEO Pharma, Front End Innovat, AS Ind Pk 55, DK-2750 Ballerup, Denmark

[3] Eli Lilly & Co, 10290 Campus Point Dr, San Diego, CA 92121 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 24期

关键词：

SESQUICILLIN; SUBGLUTINOLS; DECARBOXYLATION; MANGANESE(III); CYCLIZATIONS; SYSTEMS; FUNGUS;

D O I：

10.1021/jacs.8b04891

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A divergent strategy for assembling pyrone diterpenes is presented. Capitalizing on the unique stereo-and chemoselectivity features of radical-based chemistry, the core decalin of these structures is efficiently forged using an electrochemically assisted oxidative radical polycyclization while key peripheral substituents are appended using decarboxylative radical cross couplings. In this way, access to four natural products (subglutinols A/B, higginsianin A, and sesquicillin A) is achieved in a concise and stereocontrolled fashion that is modular and amenable to future medicinal chemistry explorations.

引用

页码：7462 / 7465

页数：4

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