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
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
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID |
---|
Dandapani, S | | | | Jeske, M | | | | Curran, DP | curran@pitt.edu | CURRAN | |
|
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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