Formal total synthesis of anti-helicobacter pylori agent (+)-spirolaxine methyl ether

TitleFormal total synthesis of anti-helicobacter pylori agent (+)-spirolaxine methyl ether
Publication TypeJournal Article
Year of Publication2016
AuthorsGadakh, SK, Sudalai, A
JournalTetrahedron Letters
Volume57
Issue1
Pagination25-28
Date PublishedJAN
ISSN0040-4039
KeywordsBrown allylation, Cu-catalyzed lactonization, Noyori's asymmetric reduction, Phthalide, Spiroketal
Abstract

A convergent, formal enantioselective synthesis of anti-Helicobacter pylori agent, (+)-spirolaxine methyl ether 2 has been achieved in high enantiomeric purity starting from commercially available 1,5-pentanediol. The strategy mainly comprises of the Noyori's asymmetric reduction and Brown allylation/Cu-catalyzed lactonization as the key step for the construction of key chiral intermediates, spiroketal 3 and phthalide fragment 4. (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2015.11.047
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.347
Divison category: 
Chemical Engineering & Process Development