Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: Formal total synthesis of (+/-)-pancracine

TitleStereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: Formal total synthesis of (+/-)-pancracine
Publication TypeJournal Article
Year of Publication2005
AuthorsPandey, G, Banerjee, P, Kumar, R, Puranik, VG
JournalOrganic Letters
Volume7
Issue17
Pagination3713-3716
Date PublishedAUG
Type of ArticleArticle
ISSN1523-7060
Abstract

[GRAPHICS] The core structure of the complex pentacyclic 5,11-methanomorphanthridine alkaloids is constructed stereospecifically in one step employing an intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The strategy is demonstrated by accomplishing the formal total synthesis of (+/-)-pancracine.

DOI10.1021/ol051321o
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry