Stereoselective Synthesis of the Tricyclic Core of (−)-Callophycoic Acid A

Autor:	Akihiro Ogura, Akihiro Sakama, Keisuke Yoshida, Ken Ichi Takao, Wataru Sumida, Yuta Unno, Yuko Motohashi, Rika Kameshima
Rok vydání:	2020
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Cyclohexane chemistry Stereochemistry Reagent Intramolecular force Organic Chemistry Stereoselectivity Ring (chemistry) Radical cyclization Stereocenter Tricyclic
Zdroj:	The Journal of Organic Chemistry. 85:3245-3264
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b03114
Popis:	Two stereocontrolled routes to the tricyclic core of (-)-callophycoic acid A are described. Our synthetic strategy relied on stereoselective allylboration using a new allylboronate reagent to construct the all-carbon quaternary stereocenter in the core, followed by efficient radical cyclization or palladium-catalyzed reductive cyclization to form its multisubstituted cyclohexane ring. The tetrahydrooxepin ring was constructed by intramolecular etheration. This study provides the first method for the stereoselective synthesis of the characteristic tricyclic skeleton of callophycoic acids.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::567ba53832ee77996b3e03a22376165a https://doi.org/10.1021/acs.joc.9b03114 Zobrazit plný text záznamu