Facile air-oxidation of N-homopiperonyl-5,6-dimethoxyhomophthalimide: simple and efficient access to nuevamine

TitleFacile air-oxidation of N-homopiperonyl-5,6-dimethoxyhomophthalimide: simple and efficient access to nuevamine
Publication TypeJournal Article
Year of Publication2008
AuthorsWakchaure, PB, Easwar, S, Puranik, VG, Argade, NP
JournalTetrahedron
Volume64
Issue8
Pagination1786-1791
Date PublishedFEB
Type of ArticleArticle
ISSN0040-4020
Abstract

A facile six-step synthesis of naturally occurring (+/-)-nuevamine with 55% overall yield has been described, starting from methyl 2-(6-formyl-2,3-dimethoxyphenyl)acetate via the quantitative benzylic air-oxidation of the corresponding N-homopiperonyl-5,6-dimethoxy-homophthalimide to N-homopiperonyl-5,6-dimethoxyisoquinoline-1,3,4-trione as the key reaction, followed by base catalyzed regioselective alcoholysis of the trione with ring contraction, acid catalyzed dehydrative ring closure of the formed lactamol and decarboxylation pathway. (C) 2007 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2007.11.104
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.645
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry