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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 H, C, and (for the Mosher esters) F NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H 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. 1 13 19 1


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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: 30 Mar 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/16188

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