Total synthesis of pachastrissamine (jaspine B) enantiomers from D-glucose

TitleTotal synthesis of pachastrissamine (jaspine B) enantiomers from D-glucose
Publication TypeJournal Article
Year of Publication2007
AuthorsRamana, CV, Giri, AG, Suryawanshi, SB, Gonnade, RG
JournalTetrahedron Letters
Volume48
Issue2
Pagination265-268
Date PublishedJAN
Type of ArticleArticle
ISSN0040-4039
Keywords4-furanose, chiron approach, Ohira-Bestmann reaction, pachastrissamine/jaspine B, pentodialdo-1, ring isomerization
Abstract

Synthesis of both enantiomers of pachastrissamine is described from a common chiral template. The stereoselective construction of the central tetrahydrofuran units was based on the pseudodesymmetrization of a pentodialdo-1,4-furanose derivative taking advantage of the latent symmetry present. (c) 2006 Published by Elsevier Ltd.

DOI10.1016/j.tetlet.2006.11.048
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.347

Divison category: 
Organic Chemistry
Physical and Materials Chemistry