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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706809
Subject(s) - forskolin , medicine , stimulation
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.