A Concise Synthesis of Forskolin | Zendy

Hylse Ondřej | Zendy; Maier Lukáš | Zendy; Kučera Roman | Zendy; Perečko Tomáš | Zendy; Svobodová Aneta | Zendy; Kubala Lukáš | Zendy; Paruch Kamil | Zendy; Švenda Jakub | Zendy

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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.

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