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

UNSPECIFIED (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
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: 08 Jan 2019 16:55
URI: http://d-scholarship.pitt.edu/id/eprint/17941

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