Total synthesis of N¹⁴-desacetoxytubulysin H

Wipf, P and Wang, Z (2007) Total synthesis of N¹⁴-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:	Creators Email Pitt Username ORCID Wipf, P pwipf@pitt.edu PWIPF 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:	12 Jun 2021 14:55
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/19840

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