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Total synthesis of (+)-nankakurines A and B and (plusmn)-5-epi-nankakurine A

Authors :
Altman, Ryan A.
Nilsson, Bradley L.
Overman, Larry E.
de Alaniz, Javier Read
Rohde, Jason M.
Taupin, Veronique
Source :
Journal of Organic Chemistry. Nov 19, 2010, Vol. 75 Issue 22, 7519-7534
Publication Year :
2010

Abstract

The first total syntheses of the Lycopodium alkaloids (+)-nankakurine A, (+)-nankakurine B and the originally supported structure of nankakurine A is feature a demanding intramolecular azomethine imine cycloaddition as the key step is reported. The reaction generated the octahydro-3,5-ethanoquinoline moiety and installed the correct relative configuration at the spiropiperidine ring juncture.

Details

Language :
English
ISSN :
00223263
Volume :
75
Issue :
22
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.243006878