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Stereoisomer libraries: Total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach

Dandapani, S and Jeske, M and Curran, DP (2004) Stereoisomer libraries: Total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach. Proceedings of the National Academy of Sciences of the United States of America, 101 (33). 12008 - 12012. ISSN 0027-8424

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Abstract

All 16 stereoisomers of the sex pheromone of pine sawfly (3,7,11-trimethylundecanol propanoate ester) have been synthesized on a 10- to 20-mg scale by a split-parallel fluorous mixture-synthesis approach. Spectral data obtained for all 32 compounds (16 alcohols and the corresponding propionates) matched well with published data, thereby validating the fluorous-tag encoding of diastereoisomers. This fluorous-tag encoding method is recommended for the efficient synthesis of multiple stereoisomers for spectroscopic studies, biological tests, or other structure-function relationships.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Dandapani, S
Jeske, M
Curran, DPcurran@pitt.eduCURRAN
Date: 17 August 2004
Date Type: Publication
Journal or Publication Title: Proceedings of the National Academy of Sciences of the United States of America
Volume: 101
Number: 33
Page Range: 12008 - 12012
DOI or Unique Handle: 10.1073/pnas.0401677101
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0027-8424
MeSH Headings: Animals; Chemistry, Organic--methods; Female; Fluorine--chemistry; Hymenoptera; Magnetic Resonance Spectroscopy; Molecular Structure; Sex Attractants--chemical synthesis; Sex Attractants--chemistry; Stereoisomerism
Other ID: NLM PMC514425
PubMed Central ID: PMC514425
PubMed ID: 15159539
Date Deposited: 30 Aug 2013 17:09
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/19722

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