A Concise Synthesis of Forskolin

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Authors

HYLSE Ondřej MAIER Lukáš KUČERA Roman PEREČKO Tomáš SVOBODOVÁ Aneta KUBALA Lukáš PARUCH Kamil ŠVENDA Jakub

Year of publication 2017
Type Article in Periodical
Magazine / Source Angewandte Chemie International Edition
MU Faculty or unit

Faculty of Science

Citation
Doi http://dx.doi.org/10.1002/anie.201706809
Field Organic chemistry
Keywords adenylyl cyclases; forskolin; natural product synthesis; structural analogues
Description 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 acidmodified Upjohn dihydroxylation of a resilient tetrasubstituted olefin. The developed route has exciting potential for the preparation of new forskolin analogues inaccessible by semisynthesis.
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