Journal of the American Chemical Society

Absolute configuration of 1, 2-disubstituted trans-cyclodecenes based on chemical correlation with (+)-dimethyl (2R)-2-butyl-2-methyloctanedioate

JA Marshall, KE Flynn

Index: Marshall, James A.; Flynn, Katherine E. Journal of the American Chemical Society, 1982 , vol. 104, # 26 p. 7430 - 7435

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Citation Number: 13

Abstract

Abstract: The absolute configuration of (-)-trans-1, 2-dimethylcyclodecene (4) has been determined to be R through chemical correlation with (+)-dimethyl (2R)-2-butyl-2- methyloctanedioate (13). Diester 13 was prepared from (+)-(4aS)-4a-methyl-2, 3, 4, 4a, 5, 6, 7, 8-octahydronaphthalen-2-one (12) through a sequence involving Eschenmoser fragmentation of the related epoxy ketone, hydrogenation of the resulting acetylenic side ...