Abstract
We will report a stereospecific route to highly potent antineoplastic agelastatin A from a readily available 1-hydroxy-4-aminocyclopentene derivative, featuring stereo- and regiospecific nitrogen functionalizations of the central cyclopentane motif to create an array of nitrogen-substituted stereogenic centers. Requisite nitrogen functionalities of the agelastatin core have been successfully installed by aziridination and subsequent regioselective azidation, leading to net stereospecific vicinal trans-diamination of the double bond. Eight manipulations in the present route that comprises 14 or 16 total steps essentially require no purifications, allowing expeditious access to the target compound.
