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Communication | Regular issue | Vol 36, No. 11, 1993, pp.2445-2450
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6509
■ Reduction of α-Pyrone Derivatives with Borane-Methyl Sulfide Complex

Takeshi Shimizu,* Sayoko Hiranuma, and Tsumoru Watanabe

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan

Abstract

Selective reduction of the 5-carbomethoxy- and 5-carbethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a-11, 19) to yield the 5-hydroxymethyl derivatives (12-18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex. Additionally, reduction of the 3-acetyl-4-hdyroxy-2H-pyran-2-one derivatives (23, 26, and 29) with borane-methyl sulfide complex afforded the binary condensed pyrone derivatives (25, 28, and 31) in good yields.