Double intramolecular oxymercuration: stereoselective synthesis of highly substituted bis-tetrahydrofuran

TitleDouble intramolecular oxymercuration: stereoselective synthesis of highly substituted bis-tetrahydrofuran
Publication TypeJournal Article
Year of Publication2006
AuthorsMohapatra, DK, Mohapatra, S, Gurjar, MK
JournalTetrahedron Letters
Volume47
Issue33
Pagination5943-5947
Date PublishedAUG
Type of ArticleArticle
ISSN0040-4039
Keywordsacetogenins, Barton-McCombie deoxygenation, demercuration, intramolecular oxymercuration, unsymmetrical bis-tetrabydrofuran, Wittig reaction
Abstract

Stereoselective intramolecular oxymercuration has been demonstrated as the key reaction for the efficient preparation of mono- and dihydroxylated unsymmetrical bis-tetrahydrofuran skeletons present in naturally occurring biologically active acetogenins using carbohydrates. These trans- and syn-selective intramolecular oxymercurations were explored in an enantio selective synthesis of the bis-tetrahydrofuran skeleton of mucoxin. (c) 2006 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2006.06.049
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.347
Divison category: 
Organic Chemistry