Triacetic Acid Lactone Methyl Ether as a Natural Products Synthon

Abstract

Deprotonation at the 6-methyl group of 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one (1d) resulted in the formation of an extended enolate (1e) which was spectroscopically identified. The utility of this enolate towards the synthesis of some natural products of polyketide origin has been described, e.g. the synthesis of 4-methoxy-6-(2-oxopropyl)-2H-pyran-2-one (4) and 4-methoxy-6-phenacyl-2H-pyran-2-one (5), the former having been isolated from Penicillium stipitatum culture, and the synthesis of 5,6-dehydrokawain (6), a natural product extracted from the wood of Aniba firmula and from the seeds of Alpina blepharocalyx.