Structural diversity through intramolecular cycloaddition and modulation of chemical reactivity in excited state. Synthesis and photoreactions of 3-oxa-tricyclo[5.2.2.0(1,5)]undecenones: novel stereoselective route to oxa-triquinanes and oxa-sterpuranes

V Singh; S Q Alam

doi:10.1016/s0960-894x(00)00503-5

Structural diversity through intramolecular cycloaddition and modulation of chemical reactivity in excited state. Synthesis and photoreactions of 3-oxa-tricyclo[5.2.2.0(1,5)]undecenones: novel stereoselective route to oxa-triquinanes and oxa-sterpuranes

Bioorg Med Chem Lett. 2000 Nov 20;10(22):2517-9. doi: 10.1016/s0960-894x(00)00503-5.

Authors

V Singh¹, S Q Alam

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay, Mumbai. vks@ether.chem.iitb.ernet.in

PMID: 11086719
DOI: 10.1016/s0960-894x(00)00503-5

Abstract

Synthesis of 11-methyl-3-oxa-tricyclo[5.2.2.0(1,5)]undecenones by intramolecular Diels-Alder reaction of highly labile spiroepoxycyclohexa-2,4-dienones and its photochemical reactions upon triplet (3T) and singlet (1S) excitation leading to a stereoselective route to oxa-triquinane and oxa-sterpurane, respectively, is described.

Publication types

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

MeSH terms

Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry*
Photochemistry

Substances

Heterocyclic Compounds