J 2017

A Concise Synthesis of Forskolin

HYLSE, Ondřej, Lukáš MAIER, Roman KUČERA, Tomáš PEREČKO, Aneta SVOBODOVÁ et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 12.102

RIV identification code

RIV/00216224:14310/17:00097892

Organization unit

Faculty of Science

UT WoS

000411810600029

Keywords in English

adenylyl cyclases; forskolin; natural product synthesis; structural analogues

Tags

Tags

International impact, Reviewed
Změněno: 10/5/2019 09:02, Mgr. Jakub Švenda, PhD.

Abstract

V originále

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 project
Name: Příprava unikátních modulátorů adenylyl cyklázy
Investor: Czech Science Foundation
LM2015043, research and development project
Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)
Investor: Ministry of Education, Youth and Sports of the CR
LM2015063, research and development project
Name: Národní infrastruktura chemické biologie (Acronym: CZ-­OPENSCREEN)
Investor: Ministry of Education, Youth and Sports of the CR
MUNI/E/0104/2017, interní kód MU
Name: Syntéza analogů forskolinu
Investor: Masaryk University, Promoting quality excellence