Chemical studies of necic acid analogues

Guthrie-Strachan, Jeffry James (1997) Chemical studies of necic acid analogues. Masters thesis, Rhodes University.

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Abstract

Various aldehydes have been reacted with methyl acrylate under Baylis-Hillman conditions, using DABCO as a catalyst, to afford a range of a-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) 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 J necine base obtained via extraction and consequent hydrolysis of retrorsine.

Item Type:Thesis (Masters)
Uncontrolled Keywords:Organic acids, Chemistry, Necis acid analogues
Subjects:Q Science > QD Chemistry
Divisions:Faculty > Faculty of Science > Chemistry
Supervisors:Kaye, Perry and Liddell, J. R.
ID Code:3294
Deposited By: Mrs Carol Perold
Deposited On:05 Sep 2012 07:47
Last Modified:05 Sep 2012 07:47
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