Journal
TETRAHEDRON LETTERS
Volume 46, Issue 3, Pages 411-414Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.11.108
Keywords
electrochemistry; anodic oxidation; hamigeran; annulation
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The tricyclic core of the hamigerans has been prepared through the use of a two-step electrochemical benzannulation reaction. The annulation proceeds through an initial conjugate addition of a phenethyl cuprate to 3-methlcyclopentenone with in situ silylation of the resulting enolate. Anodic oxidation effectively couples the pendant arene and the silyl enolether to produce a key intermediate for the synthesis of the natural products. Careful optimization revealed that the use of 'alcohol-free' conditions during the electrolysis was critical to obtain high yields of the annulated product. This method allowed the preparation. of the tricyclic core of hamigeran A and B in just four steps from commercially, available starting materials. (C) 2004 Published by Elsevier Ltd.
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