Synthesis and photoreactions of 3-oxa-tricyclo[5.2.2.0 1,5]undecenones: a novel, stereoselective route to oxa-triquinanes and oxa-sterpuranes

The synthesis of 11-methyl-3-oxa-tricyclo[5.2.2.0 1,5]undecenones and their photochemical reactions upon triplet ( 3T) and singlet ( 1S) excitation is described. Oxidation of hydroxymethylphenol gave a ketoepoxide by intramolecular cycloaddition. Manipulation of the oxirane ring furnished the chromo...

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Bibliographic Details
Published in:Tetrahedron 2002-11, Vol.58 (48), p.9729-9736
Main Authors: Singh, Vishwakarma, Alam, S.Q, Praveena, G.D
Format: Article
Language:English
Subjects:
cycloaddition
Diels–Alder reaction
oxa-polyquinanes
photo-chemistry
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Summary:The synthesis of 11-methyl-3-oxa-tricyclo[5.2.2.0 1,5]undecenones and their photochemical reactions upon triplet ( 3T) and singlet ( 1S) excitation is described. Oxidation of hydroxymethylphenol gave a ketoepoxide by intramolecular cycloaddition. Manipulation of the oxirane ring furnished the chromophoric systems. Triplet excitation of these gave tetracyclic compounds containing an oxatriquinane framework. Singlet excitation furnished the tricyclic compound having an oxasterpurane ring system in a stereoselective fashion. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01280-2