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: |
|
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-dev.library.pitt.edu/id/eprint/20500 |
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