Total synthesis and stereochemical revision of relgro and 10′-oxorelgro

Autor:	Kanakaraju Marumudi, Janardhan Gaddam, Debendra K. Mohapatra, Jhillu S. Yadav, G. Sudhakar Reddy, Ajit C. Kunwar
Rok vydání:	2019
Předmět:	Stereochemistry Chemistry Organic Chemistry Absolute configuration Total synthesis Mitsunobu reaction Physical and Theoretical Chemistry Carbon-13 NMR Optical rotation Metathesis Biochemistry Stille reaction Kinetic resolution
Zdroj:	Organic & Biomolecular Chemistry. 17:5601-5614
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c9ob00838a
Popis:	The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10'-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation and CD spectral data led to the revision of the absolute configuration at C-6' for both relgro and 10'-oxorelgro. Moreover, the 1H as well as 13C NMR data are reported for the first time for relgro.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1151f9f74589124440e6de25851675c0 https://doi.org/10.1039/c9ob00838a Zobrazit plný text záznamu