Synthesis 2016; 48(08): 1181-1190
DOI: 10.1055/s-0035-1561561
paper
© Georg Thieme Verlag Stuttgart · New York

A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization

Jyoti Prasad Mukherjee
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India   eMail: skchatto@yahoo.com
,
Suman Sil
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India   eMail: skchatto@yahoo.com
,
Amit K. Pahari
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India   eMail: skchatto@yahoo.com
,
Shital K. Chattopadhyay*
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India   eMail: skchatto@yahoo.com
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Weitere Informationen

Publikationsverlauf

Received: 26. November 2015

Accepted after revision: 11. Januar 2016

Publikationsdatum:
02. Februar 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

 
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