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Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis

Zhang, W and Luo, Z and Chen, CHT and Curran, DP (2002) Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis. Journal of the American Chemical Society, 124 (35). 10443 - 10450. ISSN 0002-7863

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Abstract

Solution-phase mixture synthesis has efficiency advantages and favorable reaction kinetics. Applications of this technique, however, have been discouraged by the difficulty in obtaining individual, pure final products by using conventional separation and identification processes. Introduced here is a new strategy for mixture synthesis that addresses the separation and identification problems. Members of a series of organic substrates are paired with a series of fluorous tags of different chain lengths. The tagged starting materials are then mixed and taken through a multistep reaction process. Fluorous chromatography is used to demix the tagged product mixtures on the basis of the fluorine content of the tags to provide the individual pure components of the mixture, which are detagged to release the final products. The utility of fluorous mixture synthesis is demonstrated by the preparation of a 560-membered library of analogues of the natural product mappicine. A seven-component mixture is carried through a four-step mixture synthesis (two one-pot and two parallel steps) to incorporate two additional points of diversity onto the tetracyclic core. Methods for analysis and purification of the intermediates are established for the quality control of the mixture synthesis.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, W
Luo, Z
Chen, CHT
Curran, DPcurran@pitt.eduCURRAN
Date: 4 September 2002
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 124
Number: 35
Page Range: 10443 - 10450
DOI or Unique Handle: 10.1021/ja026947d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Chemistry, Organic--methods; Hydrocarbons, Fluorinated--chemistry; Solutions
PubMed ID: 12197746
Date Deposited: 12 Feb 2014 23:46
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20497

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