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

作者：Mukherjee Jyoti Prasad; Sil Suman; Pahari Amit K; Chattopadhyay Shital K

来源：Synthesis (Germany), 2016, 48(8): 1181-1190.

DOI：10.1055/s-0035-1561561

• peptides
• macrocycles
• cross metathesis
• modular synthesis
• catalysis

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 beta-substituent is marginally successful with the scaffold, the corresponding reaction with an a, beta-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.

• 出版日期2016-4