Synthesis via vinyl sulfones. 38. Total synthesis of the cephalotaxus alkaloids dl-cephalotaxine, dl-11-hydroxycephalotaxine, and dl-drupacine

TP Burkholder, PL Fuchs

Index: Burkholder; Fuchs Journal of the American Chemical Society, 1990 ,  vol. 112,  # 26  p. 9601 - 9613

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Citation Number: 57

Abstract

Abstract: This paper reports the chemical details of our total synthesis of dl-cephalotaxine (1) and the completion of the first total synthesis of dl-1 I-hydroxycephalotaxine (3) and dl- drupacine (4). Key steps in the synthesis of dl-cephalotaxine include:(I) conjugate addition/alkylation of aryllithium 23C to vinyl sulfone 21 to afford adduct 24C, bearing the entire carbon assemblage;(2) self-immoliative elimination of homoallyl sulfone 24C to ...