Issue 35, 2016

Truncated borrelidin analogues: synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation

Abstract

The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.

Graphical abstract: Truncated borrelidin analogues: synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2016
Accepted
03 Aug 2016
First published
04 Aug 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 8261-8269

Truncated borrelidin analogues: synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation

T. Gündemir-Durmaz, F. Schmid, Y. El Baz, A. Häusser, C. Schneider, U. Bilitewski, G. Rauhut, D. Garnier, A. Baro and S. Laschat, Org. Biomol. Chem., 2016, 14, 8261 DOI: 10.1039/C6OB01358A

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