CH Insertion Approach to the Synthesis of e ndo, e xo-Furofuranones: Synthesis of (±)-Asarinin,(±)-Epimagnolin A, and (±)-Fargesin

RCD Brown, CJR Bataille, G Bruton…

Index: Brown; Bataille; Bruton; Hinks; Swain Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6719 - 6728

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Citation Number: 59

Abstract

A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio-and stereoselective CH insertion reactions to afford 2, 6-diaryl-3, 7-dioxabicyclo [3.3. 0] octane-8-ones (18, 26, and 36a/b) with endo, exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo, exo-furofuran lignans: ...