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Synthesis 2016; 48(08): 1181-1190
DOI: 10.1055/s-0035-1561561
DOI: 10.1055/s-0035-1561561
paper
A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization
Further Information
Publication History
Received: 26 November 2015
Accepted after revision: 11 January 2016
Publication Date:
02 February 2016 (online)
Abstract
A modular synthesis of some cyclic peptides related to a class of histone deacetylase inhibitors is reported. The synthesis utilizes a late-stage functionalization of a cyclic tetrapeptide scaffold to link the pendant alkyl chain through cross metathesis. It is observed that while the cross-metathesis reaction of a terminal olefin having a β-substituent is marginally successful with the scaffold, the corresponding reaction with an α,β-unsaturated ketone/ester is more promising. The utility of the protocol is demonstrated through the preparation of three cyclic tetrapeptides structurally related to the novel histone deacetylase inhibitors FR-225497 and trapoxin B.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561561.
- Supporting Information
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