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Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition†
Adam. J. M. Burrell,Luke Watson,Nathaniel G. Martin,Niall Oram,Iain Coldham
Organic & Biomolecular Chemistry Pub Date : 08/24/2010 00:00:00 , DOI:10.1039/C0OB00408A
Abstract

Condensation of an aldehyde with an α-amino-ester, followed by a tandem process involving cyclization to a seven-membered ring, deprotonation to an intermediate azomethine ylide and intramolecular dipolar cycloaddition gave tricyclic products related to stenine and neostenine.

Graphical abstract: Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition
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