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Communication | Special issue | Vol 5, No. 1, 1976, pp.355-365
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0355
Biosynthetic Studies with 13C: A Novel Favorsky Rearrangement Route to the Fungal Metabolite Aspyrone

Masato Tanabe,* Masakazu Uramoto, Takashi Hamasaki, and Lewis Cary

*Pharmaceytical Chemistry Department, Life Sciences Division, Stanford Research Institute, Menlo Park, California 94025, U.S.A.

Abstract

The 13C-nmr investigation of the biosynthesis of the pyrone metabolite 2-(1’,2’-epoxypropy1)-5,6-dihydro-5-hydroxy-6-methylpyran-2-one, aspyrone, isolated from A. melleus is described. Labeling distribution and incorporation level data from 1-13C-acetate, 2-13C-acetate and 1,2-13C-acetate supports a proposed Favorsky rearrangement route from a linear pentaketide unit for the biosynthesis of this fungal metabolite. 13C-nmr chemical shift assignments and carbon-carbon coupling data are presented. A Favorsky route is also proposed to account for bisfuran ring formation in aflatoxin and sterigmatocystin biosynthesis