Synthesis of Gymnoascolide A

Abstract

Recently isolated 4-benzyl-3-phenylfuran-2,5-dione and antifungal gymnoascolide A have been synthesized using the chemoselective S_N2′ coupling of phenylmagnesium bromide with dimethyl 2-(bromomethyl)fumarate, chemoselective allylic substitution of bromide in 3-(bromomethyl)-4-phenylfuran-2,5-dione with phenylmagnesium bromide and regioselective N-Selectride-induced reduction of 3-benzyl-4-phenylfuran-2,5-dione as the key reactions.

dimethyl (bromomethyl)fumarate - S_N2′ Grignard coupling reaction - functionalized maleic anhydrides - regioselective reduction - gymnoascolide A

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