A Concise Synthesis of Forskolin

被引：16

作者：

Hylse, Ondrej ^{[1
,2
]}

Maier, Lukas ^{[1
,2
]}

Kucera, Roman ^{[1
]}

Perecko, Tomas ^{[2
,3
]}

Svobodova, Aneta ^{[2
,3
]}

Kubala, Lukas ^{[2
,3
]}

Paruch, Kamil ^{[1
,2
]}

Svenda, Jakub ^{[1
,2
]}

机构：

[1] Masaryk Univ, Dept Chem, Kamenice 5, Brno 62500, Czech Republic

[2] St Annes Univ Hosp, Int Clin Res Ctr, Pekarska 53, Brno 65691, Czech Republic

[3] Acad Sci Czech Republ, Inst Biophys, Kralovopolska 135, CS-61265 Brno, Czech Republic

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 41期

关键词：

adenylyl cyclases; forskolin; natural product synthesis; structural analogues; ADENYLYL-CYCLASE ISOFORMS; KEY INTERMEDIATE; ENANTIOSELECTIVE ROUTE; ALLYLIC ALCOHOLS; (+/-)-FORSKOLIN; ACTIVATION; DIHYDROPYRAN-4-ONE; TRANSPOSITION; DERIVATIVES; INHIBITION;

D O I：

10.1002/anie.201706809

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 24-step synthesis of (+/-)-forskolin is presented, which delivered hundred milligram quantities of this complex diterpene in one pass. Transformations key to our approach include: a) a strategic allylic transposition, b) stepwise assembly of a sterically encumbered isoxazole ring, and c) citric acid-modified Upjohn dihydroxylation of a resilient tetrasubstituted olefin. The developed route has exciting potential for the preparation of new forskolin analogues inaccessible by semisynthesis.

引用

页码：12586 / 12589

页数：4

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