Synthesis of C-13 Oxidised Cuparene and Herbertane Sesquiterpenes via a Paternò-Büchi Photocyclisation-Oxetane Fragmentation Strategy: Total Synthesis of 1,13-Herbertenediol

Abstract The intramolecular Paternò-Büchi reaction of 5-aryl-4,4-dimethyl-hex-5-enals has been used to assemble the hindered cyclopentane skeleton of the cuparene and herbertane sesquiter­penes. Regioselective carbon-oxygen bond cleavage in the resulting oxetane is applied to the synthesis of 1,13-h...

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Bibliographic Details
Published in:Synlett 2004-11, Vol.2004 (13), p.2379-2381
Main Authors: Boxall, Richard J., Ferris, Leigh, Grainger, Richard S.
Format: Article
Language:English
Subjects:
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Summary:Abstract The intramolecular Paternò-Büchi reaction of 5-aryl-4,4-dimethyl-hex-5-enals has been used to assemble the hindered cyclopentane skeleton of the cuparene and herbertane sesquiter­penes. Regioselective carbon-oxygen bond cleavage in the resulting oxetane is applied to the synthesis of 1,13-herbertane diol.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-832813