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Solution-phase parallel synthesis with oligoethylene glycol sorting tags. Preparation of all four stereoisomers of the hydroxybutenolide fragment of murisolin and related acetogenins

Gudipati, V and Curran, DP and Wilcox, CS (2006) Solution-phase parallel synthesis with oligoethylene glycol sorting tags. Preparation of all four stereoisomers of the hydroxybutenolide fragment of murisolin and related acetogenins. Journal of Organic Chemistry, 71 (9). 3599 - 3607. ISSN 0022-3263

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Abstract

The principles of the oligoethylene glycol (OEG) mixture synthesis are illustrated with the synthesis of all four possible stereoisomers of a hydroxybutenolide fragment common to murisolin and many other acetogenins. Modified dimethoxybenzyl groups with varying numbers of OEG units (-CH 2CH2O-) are used to protect alcohols and serve as codes for configurations at two stereocenters. The encoded isomers are carried through several steps in a sequence of mixing prior to the reaction and then demixing during the separation to give individual pure products. A new tagging scheme is introduced in which a stereocenter bearing a hydroxy group is given two different tags. These initially redundant tags then serve to encode the configuration of another (untagged) stereocenter by appropriate pairwise reactions of the tagged precursors. The experimental features (reaction, analysis, separation, and characterization) of OEG mixture synthesis are detailed and are compared to and contrasted with those of fluorous mixture synthesis. © 2006 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Gudipati, V
Curran, DPcurran@pitt.eduCURRAN
Wilcox, CSdaylite@pitt.eduDAYLITE
Date: 28 April 2006
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 71
Number: 9
Page Range: 3599 - 3607
DOI or Unique Handle: 10.1021/jo060217x
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: 4-Butyrolactone--analogs & derivatives; 4-Butyrolactone--chemical synthesis; Acetogenins; Ethylene Glycols--chemical synthesis; Ethylene Glycols--chemistry; Fatty Alcohols--chemical synthesis; Furans--chemical synthesis; Lactones--chemical synthesis; Magnetic Resonance Spectroscopy; Stereoisomerism
PubMed ID: 16626147
Date Deposited: 17 Jun 2013 15:24
Last Modified: 17 Aug 2019 14:56
URI: http://d-scholarship.pitt.edu/id/eprint/18981

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