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Total synthesis of a 28-member stereoisomer library of murisolins

Curran, DP and Zhang, Q and Richard, C and Lu, H and Gudipati, V and Wilcox, CS (2006) Total synthesis of a 28-member stereoisomer library of murisolins. Journal of the American Chemical Society, 128 (29). 9561 - 9573. ISSN 0002-7863

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Abstract

Total syntheses of two 16-member libraries of murisolin isomers are reported. In the first library, fluorous PMB (p-methoxybenzyl) groups encode configurations, and four mixtures of four dihydroxytetrahydrofurans are prepared by Shi epoxidation followed (optionally) by Mitsunobu reaction. The mixtures are coupled by Kocienski-Julia reaction with a single hydroxybutenolide followed by hydrogenation. Demixing and detagging provide the 16 pure stereoisomers. In the second synthesis, a single mixture of four fluorous-tagged dihydroxy-tetrahydrofurans is coupled with a four-compound mixture of hydroxybutenolides that bear derivatives of DMB (dimethoxybenzyl) groups with oligoethylene glycol (OEG) units that encode the configurations at C4 and C34. The 16-compound mixture is subjected to hydrogenation, double demixing, and detagging to provide the 16 isomerically pure murisolins. Twelve of these isomers are new, while four match samples from the first library. © 2006 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Zhang, Q
Richard, C
Lu, H
Gudipati, V
Wilcox, CSdaylite@pitt.eduDAYLITE
Date: 26 July 2006
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 128
Number: 29
Page Range: 9561 - 9573
DOI or Unique Handle: 10.1021/ja061801q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Combinatorial Chemistry Techniques; Furans--chemical synthesis; Furans--chemistry; Lactones--chemical synthesis; Lactones--chemistry; Stereoisomerism
PubMed ID: 16848495
Date Deposited: 07 Jun 2013 20:40
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/18832

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