A β-hydroxyethyl carbanion equivalent

…, GR Heintzelman, SM Weinreb

Index: Klos, Andrew M.; Heintzelman, Geoffrey R.; Weinreb, Steven M. Journal of Organic Chemistry, 1997 , vol. 62, # 11 p. 3758 - 3761

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Citation Number: 13

Abstract

In the course of our ongoing work on a total synthesis of the marine hepatotoxin cylindrospermopsin, we required methodology for the formal conjugate addition of a β- hydroxyethyl moiety to an enone to produce an adduct such as 1 (eq 1). 1 Although we ultimately effected this transformation via vinyl cuprate 1, 4-addition, followed by hydroboration, we considered possible alternatives to this process, since the second step ...