A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-crispine A

Steven M Allin; Sean N Gaskell; Joannah M R Towler; Philip C Bulman Page; Basu Saha; Michael J McKenzie; William P Martin

doi:10.1021/jo071235x

A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-crispine A

J Org Chem. 2007 Nov 9;72(23):8972-5. doi: 10.1021/jo071235x. Epub 2007 Oct 9.

Authors

Steven M Allin¹, Sean N Gaskell, Joannah M R Towler, Philip C Bulman Page, Basu Saha, Michael J McKenzie, William P Martin

Affiliation

¹ Department of Chemistry and Department of Chemical Engineering, Loughborough University, Loughborough, Leicestershire, UK. s.m.allin@lboro.ac.uk

PMID: 17924694
DOI: 10.1021/jo071235x

Abstract

We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Magnetic Resonance Spectroscopy / methods
Magnetic Resonance Spectroscopy / standards
Molecular Conformation
Reference Standards
Stereoisomerism

Substances

Alkaloids
Antineoplastic Agents
Isoquinolines
crispine A