Total synthesis of (.+-.)-aphidicolin and (.+-.)-. beta.-chamigrene

…, WC Dow, JD Godfrey, S Thaisrivongs

Index: Ireland, Robert E.; Dow, William C.; Godfrey, Jollie D.; Thaisrivongs, Suvit Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1001 - 1013

Full Text: HTML

Citation Number: 47

Abstract

Total syntheses of (f)-chamigrene and (*)-aphidicolin are described. Both approaches are based on the spiroannelation of related a-methylene ketones through first hetero-Diels-Alder condensation and then Claisen rearrangement of the derived allyl vinyl ethers. A central feature of the (f)-aphidicolin synthesis is the rearrangement of the intermediate ((trimethylsily1) methyl) cyclobutanone 16 to the aphidicolane bicyclo [3.2. l] octane ring ...