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I. Total synthesis of stemonine. II. Studies towards the total synthesis of kendomycin

Posted on:2007-08-23Degree:Ph.DType:Thesis
University:Indiana UniversityCandidate:Shamim, KhalidaFull Text:PDF
GTID:2451390005984151Subject:Chemistry
Abstract/Summary:
Enantioselective total synthesis of (-)-stemonine was achieved via a convergent assembly of acyclic precursors. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an Iodine-induced tandem cyclization to construct the pyrolidino-butyrolactome framework.; The synthesis of an advanced intermediate leading towards (-)-kendomycin is described. The synthetic scheme features the application of the asymmetric conjugate addition methodology for the early generation of C13-C14 ( E)-trisubstituted olefin, providing an efficient assembly of the ansa chain. Condensation reactions probed the Julia olefination and ortho-directed metallation for attachment of the aromatic system.
Keywords/Search Tags:Total synthesis
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