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
收藏
页码：12586 / 12589
页数：4
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