Studies on the Synthesis of Furanosteroids. I. Viridin Models

Alkyne oxazoles of general structure I are transformed directly to furo[2,3-b]phenol derivatives II by a sequence involving intramolecular Diels−Alder/retro-Diels−Alder reaction followed by tautomerization. Suitably functionalized phenols II undergo an intramolecular phenol−dienone−aldol condensatio...

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Bibliographic Details
Published in:Organic letters 2006-08, Vol.8 (18), p.4125-4128
Main Authors: Sessions, E. Hampton, Jacobi, Peter A
Format: Article
Language:English
Subjects:
Androstenes - chemistry
Bacteriocins - chemistry
Furans - chemistry
Molecular Structure
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Summary:Alkyne oxazoles of general structure I are transformed directly to furo[2,3-b]phenol derivatives II by a sequence involving intramolecular Diels−Alder/retro-Diels−Alder reaction followed by tautomerization. Suitably functionalized phenols II undergo an intramolecular phenol−dienone−aldol condensation, generating the A,B,E-ring skeleton III characteristic of the viridin (1) class of furanosteroids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061697h