A Versatile Stereoselective Synthesis of e ndo, e xo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

NA Swain, RCD Brown, G Bruton

文献索引：Swain, Nigel A.; Brown, Richard C. D.; Bruton, Gordon Journal of Organic Chemistry, 2004 , vol. 69, # 1 p. 122 - 129

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被引用次数: 46

摘要

A new stereoselective route to endo, exo-2, 6-diarylfurofuranones has been developed using Mn (III)-mediated intramolecular cyclopropanation and CH insertion reactions as key CC bond-forming steps. Mn (III)-mediated oxidative cyclization of acetoacetate derivative 11 afforded 1-acetyl-4-aryl-3-oxabicyclo [3.1. 0] hexan-2-one (12) with excellent diastereocontrol (dr 22: 1). Subsequent Lewis acid-catalyzed opening of the activated ...