Tetraquinanes via [4 + 4] photocycloaddition/transannular ring closure

Peiling Chen; Patrick J Carroll; Scott McN Sieburth

doi:10.1021/ol101802s

Tetraquinanes via [4 + 4] photocycloaddition/transannular ring closure

Org Lett. 2010 Oct 15;12(20):4510-2. doi: 10.1021/ol101802s.

Authors

Peiling Chen¹, Patrick J Carroll, Scott McN Sieburth

Affiliation

¹ Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.

PMID: 20857951
DOI: 10.1021/ol101802s

Abstract

Intramolecular [4 + 4] photocycloaddition of a furan and a cyclopentane-annulated 2-pyridone yields a cyclooctadiene product with four new stereogenic centers. Transannular ring closure produces the 5-5-5-5 fused ring system of the crinipellins, including three contiguous quaternary carbons, with the correct absolute stereochemistry derived from (-)-carvone.