Details of the synthesis of the methyl ester of the side chain of homoharringtonine, a natural product with antileukemic properties, are reported below. The key tactical element involved a Michael addition between the known chiral imine 4 and 2‐acetoxyacrylonitrile (5), furnishing the adduct (2R,1′R)‐6 with a high degree of regio‐ and stereoselectivity. This adduct was then converted into the target compound (R)‐2 by a linear sequence of ten chemical operations, in 6.0% overall yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Keller et al. (2003) studied this question.
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