Synthesis and reactions of cyclopentadiene monoaziridine: a concise approach to the core of agelastatin A

An improved protocol for the preparation of cyclopentadiene monoaziridine is described (88% yield). The utility of cyclopentadiene monoaziridine is demonstrated by its use in (i) the shortest synthetic entry into 4-amino substituted cyclopentenes and (ii) the preparation of two key intermediates in a concise synthetic approach to the cyclopentane core of agelastatin A. The agelastatin A model studies make use of a lithium amide-mediated epoxide to allylic alcohol rearrangement reaction.