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Synthesis and spectroscopic analysis of a stereoisomer library of the phytophthora mating hormone α1 and derived bis-Mosher esters

Bajpai, R and Curran, DP (2011) Synthesis and spectroscopic analysis of a stereoisomer library of the phytophthora mating hormone α1 and derived bis-Mosher esters. Journal of the American Chemical Society, 133 (50). 20435 - 20443. ISSN 0002-7863

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Abstract

Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone α1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of 1H, 13C, and (for the Mosher esters) 19F NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the 1H NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed. © 2011 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Bajpai, R
Curran, DPcurran@pitt.eduCURRAN
Date: 21 December 2011
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 133
Number: 50
Page Range: 20435 - 20443
DOI or Unique Handle: 10.1021/ja2082679
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Esters; Hormones--chemical synthesis; Hormones--chemistry; Nuclear Magnetic Resonance, Biomolecular; Phytophthora--chemistry; Stereoisomerism
Other ID: NLM NIHMS338085 [Available on 12/21/12], NLM PMC3241891 [Available on 12/21/12]
PubMed Central ID: PMC3241891
PubMed ID: 22047536
Date Deposited: 06 Nov 2012 18:28
Last Modified: 22 Jun 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/16188

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