An alternative synthesis of Dolby-Weinreb enamine en route to cephalotaxine

BC Ma, YQ Wang, WDZ Li

Index: Ma, Bao-Chun; Wang, Yong-Qiang; Li, Wei-Dong Z. Journal of Organic Chemistry, 2005 , vol. 70, # 11 p. 4528 - 4530

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Citation Number: 15

Abstract

Dolby−Weinreb enamine (2), a benzazepine heterocycle, has been a key advanced intermediate in the classical Weinreb synthesis 1 of cephalotaxine (CET, 1), which is the core structure of the structurally unique antileukemia Cephalotaxus alkaloid ester derivatives. 2 Enamine 2 was also synthesized by other groups 3 following the pioneering works by Dolby and Weinreb in this field, via different annulation approaches, as outlined in Figure 1, respectively.