A concise route to the azaspirodecane moiety of halichlorine and structurally related alkaloids

Andrea L de Sousa; Ronaldo A Pilli

doi:10.1021/ol050306g

A concise route to the azaspirodecane moiety of halichlorine and structurally related alkaloids

Org Lett. 2005 Apr 14;7(8):1617-9. doi: 10.1021/ol050306g.

Authors

Andrea L de Sousa¹, Ronaldo A Pilli

Affiliation

¹ Instituto de Química, Universidade Estadual de Campinas, C. P. 6154,13084-971, Campinas, SP, Brazil.

PMID: 15816766
DOI: 10.1021/ol050306g

Abstract

[reaction: see text] A tandem Michael addition-enolate alkylation followed by Dieckmann cyclization and Beckmann rearrangement provided the corresponding [5.4.0] azaspirobicyclodecane, a key intermediate in our synthetic route to the marine alkaloid halichlorine (1).

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Animals
Molecular Structure
Porifera / chemistry
Spiro Compounds / chemical synthesis*
Stereoisomerism

Substances

Alkaloids
Spiro Compounds
halichlorine