Studies directed towards the total synthesis of (-)-reiswigin A via enantioselective deprotonation.

摘要

As a testing ground for the practical application of asymmetric synthesis (−)-reiswigin A, a potent antiviral agent, was chosen as a target for total synthesis. The key asymmetric step, enantioselective deprotonation of an intermediate meso-bicyclic ketone using a chiral lithium amide base, routinely gave ee's in the range of 90–94%, establishing 3 of the 4 chiral centers in one step. Advanced intermediates in the synthesis of reiswigin A have been generated, along with an epimer of this targeted natural product.