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Binary fluorous tagging enables the synthesis and separation of a 16-stereoisomer library of macrosphelides

Curran, DP and Sinha, MK and Zhang, K and Sabatini, JJ and Cho, DH (2012) Binary fluorous tagging enables the synthesis and separation of a 16-stereoisomer library of macrosphelides. Nature Chemistry, 4 (2). 124 - 129. ISSN 1755-4330

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Abstract

Fluorous mixture synthesis minimizes the effort to synthesize small-molecule libraries by labelling the molecules rather than the reaction vessels. Reactants are labelled with fluorinated tags and products can later be demixed based on the fluorine content. A limit in the number of available tags can be overcome by using binary encoding so that a total of four tags can label uniquely a library of 16 compounds. This strategy, however, means that separation based on fluorine content alone is not possible. Here, we solve this problem by selectively removing one tag after an initial demixing step; a second demixing provides each individual compound. The usefulness of this strategy is demonstrated by the synthesis of a library that contains all 16 diastereomers of the natural products macrosphelides A and E. Macrosphelide D was not in this library, and so its assigned structure was incorrect. We determined its constitution by using NMR spectroscopy and its configuration by synthesizing four candidate stereoisomers. © 2012 Macmillan Publishers Limited. All rights reserved.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Sinha, MK
Zhang, K
Sabatini, JJ
Cho, DH
Date: 1 February 2012
Date Type: Publication
Journal or Publication Title: Nature Chemistry
Volume: 4
Number: 2
Page Range: 124 - 129
DOI or Unique Handle: 10.1038/nchem.1233
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1755-4330
MeSH Headings: Fluorine--chemistry; Small Molecule Libraries--chemical synthesis; Small Molecule Libraries--isolation & purification; Stereoisomerism
Other ID: NLM NIHMS340049, NLM PMC3269761
PubMed Central ID: PMC3269761
PubMed ID: 22270645
Date Deposited: 01 Apr 2013 20:18
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/18031

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