Synthesis of Termini-Differentiated 6-Carbon Stereotetrads: An Alkylative Oxidation Strategy for Preparation of the C21−C26 Segment of Apoptolidin1

Autor:	Philip L. Fuchs, Yuzhong Chen, Eduardo Torres, Jerry B. Evarts
Rok vydání:	2002
Předmět:	Stereochemistry Jacobsen epoxidation Organic Chemistry Epoxide Sequence (biology) Biochemistry Redox Sulfone Catalysis chemistry.chemical_compound Enantiopure drug chemistry Moiety Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 4:3571-3574
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol026377m
Popis:	[reaction: see text] Two methods have been developed for the synthesis of epoxide 36. The first uses (+)-pulegone 25 as an enantiopure starting material and introduces the requisite intricacy of target 22 in 12 operations. The second method employs an enantiospecific catalytic Jacobsen epoxidation of 1a and is five operations shorter. The second sequence features an oxygen-directed alkylative oxidation reaction that re-establishes the dienyl sulfone functionality with concomitant 1,3-transposition of the sulfone moiety.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c66fc79f4aaffd9693ce02bb8aae8e91 https://doi.org/10.1021/ol026377m Zobrazit plný text záznamu