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Synthesis 2008(1): 26-28
DOI: 10.1055/s-2007-990901
DOI: 10.1055/s-2007-990901
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Gymnoascolide A
Further Information
Received
14 September 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)
Abstract
Recently isolated 4-benzyl-3-phenylfuran-2,5-dione and antifungal gymnoascolide A have been synthesized using the chemoselective SN2′ 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.
Key words
dimethyl (bromomethyl)fumarate - SN2′ Grignard coupling reaction - functionalized maleic anhydrides - regioselective reduction - gymnoascolide A
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