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Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis

Curran, DP and Furukawa, T (2002) Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis. Organic Letters, 4 (13). 2233 - 2235. ISSN 1523-7060

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Abstract

(matrix presented) Four analogues made in one synthesis Four truncated analogues of the natural product discodermolide were synthesized in a single synthetic sequence. Precursors bearing four different groups at C22, each with a unique fluorous p-methoxybenzyl substituent on the C17 hydroxy group, were mixed and taken through an nine-step sequence. Demixing by fluorous chromatography followed by deprotection and purification provided the individual analogues in 3-7% overall yields and with a savings of 24 synthetic steps. Fluorous mixture synthesis is recommended as a new technique to make multiple natural product analogues in a single multistep synthesis.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Furukawa, T
Date: 27 June 2002
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 4
Number: 13
Page Range: 2233 - 2235
DOI or Unique Handle: 10.1021/ol026084t
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkanes; Antineoplastic Agents--chemical synthesis; Antineoplastic Agents--isolation & purification; Carbamates; Chromatography; Fluorine; Hydrocarbons, Fluorinated--chemistry; Lactones--chemical synthesis; Lactones--isolation & purification; Pyrones
PubMed ID: 12074675
Date Deposited: 12 Feb 2014 23:44
Last Modified: 15 Oct 2017 06:55
URI: http://d-scholarship.pitt.edu/id/eprint/20500

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