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Total synthesis of N<sup>14</sup>-desacetoxytubulysin H

Wipf, P and Wang, Z (2007) Total synthesis of N<sup>14</sup>-desacetoxytubulysin H. Organic Letters, 9 (8). 1605 - 1607. ISSN 1523-7060

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Abstract

Equation presented The N14-desacetoxy analogue of tubulysin H was prepared in 20 steps and 2.1% overall yield. Our strategy features a thiazole anion addition to assemble the tubuvaline residue at the C(10)-C(11) bond, as well as acylations at N5, N14, and N 17. This iterative coupling approach, as well as the removal of the labile N,O-acetal at N14, enables the synthesis of analogues for detailed studies of structure-activity relationships in this family of potent tubulin disrupters. © 2007 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Wang, Z
Date: 12 April 2007
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 9
Number: 8
Page Range: 1605 - 1607
DOI or Unique Handle: 10.1021/ol070415q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Molecular Structure; Oligopeptides--chemical synthesis; Oligopeptides--chemistry; Organic Chemicals--chemical synthesis; Organic Chemicals--chemistry
PubMed ID: 17367155
Date Deposited: 09 Oct 2013 16:05
Last Modified: 26 Jan 2019 10:55
URI: http://d-scholarship.pitt.edu/id/eprint/19840

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