147950-83-2Relevant academic research and scientific papers
A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization
Mukherjee, Jyoti Prasad,Sil, Suman,Pahari, Amit K.,Chattopadhyay, Shital K.
, p. 1181 - 1190 (2016)
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.
N-Alkenyl Nitrone Dipolar Cycloaddition Routes to Piperidines and Indolizidines. Part 5. Preparation of a Gephyrotoxin Precursor
Holmes, Andrew B.,Hughes, Andrew B.,Smith, Adrian L.
, p. 633 - 644 (2007/10/02)
The synthesis of the B/C indolizidine ring skeleton of the alkaloid gephyrotoxin 3 is described.The route involved oxidative cleavage of the racemic bicyclic isoxazolidine 2 to form the nitrone 4 and its dipolar addition with methyl acrylate to give the a
