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

Posted on:2002-05-24Degree:Ph.DType:Thesis
University:The University of New Brunswick (Canada)Candidate:Shannon, Dean EverettFull Text:PDF
GTID:2461390011999747Subject:Chemistry
Abstract/Summary:
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.
Keywords/Search Tags:Synthesis
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