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The unusual [5.3.2]bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellins A and B has been synthesized for the first time by a sequence of Sharpless dihydroxylation, ring-closing metathesis (RCM), and intramolecular Heck reaction (see scheme). The asymmetric synthesis of the 1-epi aglycon proceeds with virtually complete diastereo- and enantioselectivity (≥98 % de, ≥98 % ee) in 13 steps and an overall yield of 5.6 %.
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Enders et al. (2005) studied this question.
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