Underappreciated and neglected, isoxazoles are extremely good at stabilizing α cations. This ability is exploited in a method for the stereocontrolled introduction of angular substituents as found in polyketide-derived polycyclic natural products, such as 1. In a two-step process, the stereoselective addition of a nucleophile to the ketol 2 is followed by a regio- and stereospecific pinacol rearrangement. Bn=benzyl; R=allyl, aryl, heteroaryl, vinyl.
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Suzuki et al. (2007) studied this question.
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