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Efforts towards the total synthesis of (+)-sorangicin A

Posted on:2010-09-09Degree:Ph.DType:Thesis
University:The University of North Carolina at Chapel HillCandidate:Haley, Matthew WFull Text:PDF
GTID:2441390002974611Subject:Chemistry
Abstract/Summary:
Efforts towards (+)-sorangicin A, a previously unprepared antibiotic macrolide, are reported. A modular approach which investigates several coupling strategies for the union of three core cyclic ether fragments was utilized. The bicyclic ether and tetrahydropyran moieties were constructed utilizing a ring-closing/epoxide opening strategy while the dihydropyran subunit relied on a ring-closing metathesis for the formation of the heterocycle. The three core synthetic fragments were elaborated to various synthetic intermediates and several coupling strategies were evaluated.
Keywords/Search Tags:Several coupling strategies, Three core
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