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Total syntheses of (+/-)-isophellibiline and (+/-)-communesin F, and design, synthesis and pharmacological evaluation of dihydro-beta-erythroidine (DHbetaE) analogs

Posted on:2013-01-22Degree:Ph.DType:Thesis
University:The Pennsylvania State UniversityCandidate:Belmar, JohannesFull Text:PDF
GTID:2451390008980008Subject:Chemistry
Abstract/Summary:
The intramolecular cycloaddition reactions of 2-amidoacroleins are discussed in Part I. Application of this methodology in natural product synthesis resulted in the first total synthesis of a member of the nonaromatic homoerythrinan class of natural products, (+/-)-isophellibiline. The synthesis was completed in 16 linear steps from 2,2-dimethyl-1,3-dioxan-5-one in an overall yield of 2.3%. In addition, the design, synthesis and pharmacological evaluation of analogs of the nicotinic acetylcholine receptor (nAChR) antagonist dihydro-beta-erythroidine (DHbetaE) are described.;In Part II efforts towards the total synthesis of the marine natural product (+/-)-communesin F are discussed. First, we describe the reactions of aza-ortho-xylylenes generated via the Lewis acid catalyzed retrocycloaddition reaction of 3,1-benzoxazin-2-ones. Although, the total synthesis of communesin F was not realized through application of this methodology, it resulted in the preparation of an advanced intermediate towards communesin F.;Next, we explore the Diels--Alder cycloaddition reactions of indol-2-one and detail the successfully applied this methodology in a concise total synthesis of (+/-)-communesin F. The synthesis was completed in 15 linear steps from 4-bromotryptophol in an overall yield of 6.7%.
Keywords/Search Tags:Synthesis, -communesin, Total
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