Regioselective NaBH4 and DIBAL-H reductions of 3,4-dimethoxyhomopiperonylphthalimide: concise and efficient synthesis of nuevamine and isonuevamine

TitleRegioselective NaBH4 and DIBAL-H reductions of 3,4-dimethoxyhomopiperonylphthalimide: concise and efficient synthesis of nuevamine and isonuevamine
Publication TypeJournal Article
Year of Publication2011
AuthorsWakchaure, PB, Kunte, SS, Argade, NP
JournalIndian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry
Volume50
Issue6
Pagination868-871
Date PublishedJUN
ISSN0376-4699
Keywords6-dimethoxyhomophthalimide, intramolecular dehydrative cyclizations, isonuevamine, N-Homopiperonyl-5, nuevamine, regioselective reductions, synthesis
Abstract

Facile synthesis of nuevamine and isonuevamine has been reported via the regioselectivc reduction of hindered and unhindered carbonyl groups of 3,4-dimethoxyhomopiperonylphthalimide, respectively using sodium borohydridc and diisobutylaluminum hydride, Mowed by an acid catalyzed intramolecular dehydrative cyclization pathways. The chemistry involved in obtaining the regioselectivity has been discussed in brief.

Type of Journal (Indian or Foreign)

Indian

Impact Factor (IF)0.891
Divison category: 
Organic Chemistry