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A Concise Route to α′‐Methoxy‐γ‐pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′‐Dimethoxy‐γ‐pyrone
Author(s) -
De Paolis Michaël,
Rosso Helèna,
Henrot Matthias,
Prandi Cristina,
d'Herouville Florent,
Maddaluno Jacques
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001780
Subject(s) - desymmetrization , pyrone , computer science , chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
Two steps is the rule : A concise synthesis of versatile α′‐methoxy‐γ‐pyrones (see scheme) is described that uses an innovative desymmetrization of α,α′‐dimethoxy‐γ‐pyrone, relying upon conjugate addition of nucleophiles. This new strategy is applied to the preparation of α‐methyl‐ and α‐carboxaldehyde‐α′‐methoxy‐γ‐pyrones and to a short synthesis of verticipyrone.