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Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones - Tools and tactics for solving problems in fluorous mixture synthesis

Dandapani, S and Jeske, M and Curran, DP (2005) Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones - Tools and tactics for solving problems in fluorous mixture synthesis. Journal of Organic Chemistry, 70 (23). 9447 - 9462. ISSN 0022-3263

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Abstract

The application of fluorous mixture synthesis (FMS) for accessing natural products and their stereoisomers was validated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone. Four fluorous p-methoxybenzyl groups were used as tags, and a "4-mix-4-split" approach was employed in a divergent synthesis. This paper presents the details of the FMS of pine sawfly sex pheromones with an emphasis on identification and solving of problems encountered when working with fluorous mixtures. © 2005 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Dandapani, S
Jeske, M
Curran, DPcurran@pitt.eduCURRAN
Date: 11 November 2005
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 70
Number: 23
Page Range: 9447 - 9462
DOI or Unique Handle: 10.1021/jo051526a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Animals; Chemistry, Organic--methods; Female; Fluorine--chemistry; Hymenoptera--chemistry; Sex Attractants--chemical synthesis; Sex Attractants--chemistry; Stereoisomerism
PubMed ID: 16268620
Date Deposited: 03 Jul 2013 15:48
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/19250

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