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Minimal fluorous tagging strategy that enables the synthesis of the complete stereoisomer library of SCH725674 macrolactones

Moretti, JD and Wang, X and Curran, DP (2012) Minimal fluorous tagging strategy that enables the synthesis of the complete stereoisomer library of SCH725674 macrolactones. Journal of the American Chemical Society, 134 (18). 7963 - 7970. ISSN 0002-7863

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Abstract

Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags-one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14- pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra. © 2012 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Moretti, JD
Wang, X
Curran, DPcurran@pitt.eduCURRAN
Date: 9 May 2012
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 134
Number: 18
Page Range: 7963 - 7970
DOI or Unique Handle: 10.1021/ja302260d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Antifungal Agents--chemical synthesis; Antifungal Agents--chemistry; Aspergillus--chemistry; Halogenation; Lactones--chemical synthesis; Lactones--chemistry; Macrocyclic Compounds--chemical synthesis; Macrocyclic Compounds--chemistry; Stereoisomerism
Other ID: NLM NIHMS372947 [Available on 05/09/13], NLM PMC3356113 [Available on 05/09/13]
PubMed Central ID: PMC3356113
PubMed ID: 22515682
Date Deposited: 29 Mar 2013 15:50
Last Modified: 05 Feb 2019 16:55
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/17941

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