0485514 - BFÚ 2018 RIV DE eng J - Článek v odborném periodiku
Hylse, O. - Maier, L. - Kučera, R. - Perečko, Tomáš - Svobodová, Aneta - Kubala, Lukáš - Paruch, K. - Svenda, J.
A Concise Synthesis of Forskolin.
Angewandte Chemie - International Edition. Roč. 56, č. 41 (2017), s. 12586-12589. ISSN 1433-7851. E-ISSN 1521-3773
Institucionální podpora: RVO:68081707
Klíčová slova: adenylyl-cyclase isoforms * key intermediate * enantioselective route
Obor OECD: Biochemistry and molecular biology
Impakt faktor: 12.102, rok: 2017 ; AIS: 3.376, rok: 2017
DOI: https://doi.org/10.1002/anie.201706809

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.
Trvalý link: http://hdl.handle.net/11104/0280506