Studies toward the total synthesis of the cytotoxic sponge alkaloid pyrinodemin A

J E Baldwin; S P Romeril; V Lee; T D Claridge

doi:10.1021/ol015646q

Studies toward the total synthesis of the cytotoxic sponge alkaloid pyrinodemin A

Org Lett. 2001 Apr 19;3(8):1145-8. doi: 10.1021/ol015646q.

Authors

J E Baldwin¹, S P Romeril, V Lee, T D Claridge

Affiliation

¹ The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. jack.baldwin@chem.ox.ac.uk

PMID: 11348180
DOI: 10.1021/ol015646q

Abstract

[structure: see text]. The syntheses of the proposed structure of pyrinodemin A (1) and its cis double bond positional isomer (C15'-C16') in racemic form are described. The key reaction involved an intramolecular nitrone/double bond cycloaddition. Our results suggest that neither 1 nor its double positional isomer is the correct structure of pyrinodemin A

Publication types

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

MeSH terms

Alkaloids / chemistry*
Magnetic Resonance Spectroscopy
Models, Chemical
Oxazoles / chemical synthesis*
Pyridines / chemical synthesis*
Stereoisomerism

Substances

Alkaloids
Oxazoles
Pyridines
pyrinodemin A