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 condensation, generating the A,B,E-ring skeleton III characteristic of the viridin (1) class of furanosteroids.
Sessions
E Hampton
EH
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.
Jacobi
Peter A
PA
D000736:Androstenes / Q000737:chemistry*; D001430:Bacteriocins / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure
D000736:Androstenes; D001430:Bacteriocins; D005663:Furans; C012097:viridin