Chemical studies of necic acid analogues

Guthrie-Strachan, Jeffry James

Title: Chemical studies of necic acid analogues
Creator: Guthrie-Strachan, Jeffry James
ThesisAdvisor: Kaye, Perry T
ThesisAdvisor: Liddell, J. R.
Subject: Organic acids
Subject: Chemistry, Organic
Date: 1997
Type: Thesis
Type: Masters
Type: MSc
Identifier: vital:4425
Identifier: http://hdl.handle.net/10962/d1006909
Identifier: Organic acids
Identifier: Chemistry, Organic
Description: Various aldehydes have been reacted with methyl acrylate under Baylis-Hillman conditions, using DABCO as a catalyst, to afford a range of α-substituted acrylic esters containing an allylic hydroxy group. Selected Baylis-Hillman products have been brominated, hydrolysed and acetylated to afford substrates for the synthesis of necic acid analogues. The diastereo- and regioselectivity of nucleophilic attack, using sodium methylmercaptan, on the Baylis-Hillman products and selected brominated derivatives was investigated. The allylic hydroxy compounds favour conjugate addition with the generation of a new chiral centre, while the allylic bromo derivatives favour substitution (SN and SN') (S[subscript N] and S[subscript N]') with consequent loss of chirality. (E)-2-Isopropylcrotonic acid, a vital precursor in the synthesis of all stereoisomers of trachelanthic and viridifloric acid, was synthesised in an attempt to obtain the necic acid components required for total alkaloid synthesis of lycopsamine and its derivatives. This precursor and salicylic acid were then used to prepare esters of retronecine, a dihydroxy necine base obtained via extraction and consequent hydrolysis of retrorsine.
Format: 100 p., pdf
Publisher: Rhodes University, Faculty of Science, Chemistry
Language: English
Rights: Guthrie-Strachan, Jeffry James

Hits: 1076
Visitors: 1162
Downloads: 124

Collections

RU Department of Chemistry

		Thumbnail	File	Description	Size	Format
View Details Download			SOURCEPDF	PDF	2 MB	Adobe Acrobat PDF	View Details Download