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Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers

Sui, B and Yeh, EAH and Curran, DP (2010) Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers. Journal of Organic Chemistry, 75 (9). 2942 - 2954. ISSN 0022-3263

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Two different mixture synthesis routes have been used to make the four stereoisomers of petrocortyne A. A first quick and dirty route provided a mixture of the four isomers in nonselective fashion. Mosher and 2-naphthylmethoxyacetic acid (NMA) ester methods were developed to identify the components, and the mixture was partially resolved on analytical chiral HPLC to give the two pure enantiomers of petrocortyne A and the racemate of its diastereomer. A second fluorous mixture synthesis produced all four isomers of petrocortyne A in individual pure form. Comparison of spectra of Mosher derivatives of the synthetic isomers with two supposedly different natural products showed that both natural samples were instead identical and had the (3S,14S) configuration. Likewise, petrocortynes B, D, and F-H are (3S,14S) and petrocortyne D is (3R,14S). Having access to all possible candidate isomers of both petrocortyne A and its Mosher derivatives provided a secure structure assignment not so much because one of the isomers matched the natural product, but because all of the other isomers did not. © 2010 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Sui, B
Yeh, EAH
Curran, DPcurran@pitt.eduCURRAN
Date: 7 May 2010
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 75
Number: 9
Page Range: 2942 - 2954
DOI or Unique Handle: 10.1021/jo100115h
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Acetates--chemistry; Animals; Biological Agents--chemical synthesis; Esters--chemistry; Fatty Alcohols--chemical synthesis; Molecular Structure; Petrosia--chemistry; Phenylacetates--chemistry; Stereoisomerism
Other ID: NLM NIHMS196959, NLM PMC2871111
PubMed Central ID: PMC2871111
PubMed ID: 20394446
Date Deposited: 12 Feb 2013 15:09
Last Modified: 02 Feb 2019 15:58


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