Carbohydrate-based synthesis of the C13-C22 fragment of amphidinolide X

TitleCarbohydrate-based synthesis of the C13-C22 fragment of amphidinolide X
Publication TypeJournal Article
Year of Publication2012
AuthorsGurjar, MK, Yellol, GS, Mohapatra, DK
JournalEuropean Journal of Organic Chemistry
Issue9
Pagination1753-1758
Date PublishedMAR
ISSN1434-193X
KeywordsCytotoxicity, Macrolides, Mitsunobu inversion, Natural products, Wittig reactions
Abstract

A facile carbohydrate-based route was developed for the synthesis of the tetrahydrofuran (C13C22) fragment of amphidinolide X. Starting from L-sorbose, the key reactions followed include the stereoselective synthesis of a quaternary center at C1, BartonMcCombie deoxygenation at C2, Mitsunobu inversion at C3, and chain elongation by a Wittig reaction at C5.

DOI10.1002/ejoc.201101605
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.344
Divison category: 
Organic Chemistry