A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition.

Autor: Uosis-Martin M; Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom., Pantoş GD, Mahon MF, Lewis SE
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2013 Jun 21; Vol. 78 (12), pp. 6253-63. Date of Electronic Publication: 2013 Jun 10.
DOI: 10.1021/jo401014n
Abstrakt: A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.
Databáze: MEDLINE