Synthesis of an analogue of the marine polypropionate tridachiahydropyrone.
[reaction: see text] A novel approach to the formation of the unusual pyrone-containing ring systems as found in polypropionate metabolites from the Tridachia family of marine molluscs has been developed. This approach includes an intramolecular cyclization of a beta-keto acid onto a cyclohexenone ring to afford a fused, bicyclic pyrone.
Jeffery
David W
DW
School of Chemistry, Physics and Earth Sciences, Flinders University, G. P. O. Box 2100, S.A. 5001, Australia.
Perkins
Michael V
MV
White
Jonathan M
JM
D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D007651:Keto Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D008974:Mollusca / Q000737:chemistry; D010084:Oxidation-Reduction; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D007651:Keto Acids; D011753:Pyrones; C507269:tridachiahydropyrone