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The first total synthesis of (-)-lemonomycin and progress toward the total synthesis of (+)-cyanocycline A

Posted on:2007-08-06Degree:Ph.DType:Thesis
University:California Institute of TechnologyCandidate:Ashley, Eric RobertFull Text:PDF
GTID:2451390005486299Subject:Chemistry
Abstract/Summary:
The first total synthesis of (-)-lemonomycin has been accomplished. The synthesis features a novel, auxiliary-controlled asymmetric dipolar cycloaddition, a highly convergent Suzuki coupling, a diastereoselective enamide hydrogenation to set the C(3) stereochemistry, and a convergent, efficient, and completely diastereoselective Pictet-Spengler cyclization with a glycosyloxy acetaldehyde.; The total synthesis of (+)-cyanocycline A has been approached along two routes. Both routes feature dipolar cycloaddition reactions with alkyne-containing substrates and completely diastereoselective hydrogenations to set the C(4) stereochemistry. Proposals for the advancement of late-stage intermediates to the natural product are included.
Keywords/Search Tags:Total synthesis
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