HYLSE, Ondřej, Lukáš MAIER, Roman KUČERA, Tomáš PEREČKO, Aneta SVOBODOVÁ, Lukáš KUBALA, Kamil PARUCH and Jakub ŠVENDA. A Concise Synthesis of Forskolin. Angewandte Chemie International Edition. Německo: Verlag Chemie, vol. 2017, No 56, p. 12586-12589. ISSN 1433-7851. doi:10.1002/anie.201706809. 2017.
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Basic information
Original name A Concise Synthesis of Forskolin
Authors HYLSE, Ondřej (203 Czech Republic, belonging to the institution), Lukáš MAIER (203 Czech Republic, belonging to the institution), Roman KUČERA (703 Slovakia, belonging to the institution), Tomáš PEREČKO (703 Slovakia), Aneta SVOBODOVÁ (203 Czech Republic), Lukáš KUBALA (203 Czech Republic), Kamil PARUCH (203 Czech Republic, guarantor, belonging to the institution) and Jakub ŠVENDA (203 Czech Republic, belonging to the institution).
Edition Angewandte Chemie International Edition, Německo, Verlag Chemie, 2017, 1433-7851.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher Germany
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 12.102
RIV identification code RIV/00216224:14310/17:00097892
Organization unit Faculty of Science
Doi http://dx.doi.org/10.1002/anie.201706809
UT WoS 000411810600029
Keywords in English adenylyl cyclases; forskolin; natural product synthesis; structural analogues
Tags NZ
Tags International impact, Reviewed
Changed by Changed by: Mgr. Jakub Švenda, PhD., učo 43501. Changed: 10/5/2019 09:02.
Abstract
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.
Links
GJ15-10504Y, research and development projectName: Příprava unikátních modulátorů adenylyl cyklázy
Investor: Czech Science Foundation
LM2015043, research and development projectName: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)
Investor: Ministry of Education, Youth and Sports of the CR
LM2015063, research and development projectName: Národní infrastruktura chemické biologie (Acronym: CZ-­OPENSCREEN)
Investor: Ministry of Education, Youth and Sports of the CR
MUNI/E/0104/2017, interní kód MUName: Syntéza analogů forskolinu
Investor: Masaryk University, Promoting quality excellence
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