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.
Related projects:	Příprava unikátních modulátorů adenylyl cyklázy Czech Infrastructure for Integrative Structural Biology CZ-OPENSCREEN: National Infrastructure for Chemical Biology Syntéza analogů forskolinu