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A Concise Synthesis of Forskolin
Author(s) -
Hylse Ondřej,
Maier Lukáš,
Kučera Roman,
Perečko Tomáš,
Svobodová Aneta,
Kubala Lukáš,
Paruch Kamil,
Švenda Jakub
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706809
Subject(s) - semisynthesis , forskolin , chemistry , dihydroxylation , diterpene , olefin fiber , stereochemistry , isoxazole , ring (chemistry) , combinatorial chemistry , enantioselective synthesis , organic chemistry , biochemistry , catalysis , receptor
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.