Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent

K Akaji, S Aimoto

Index: Akaji, Kenichi; Aimoto, Saburou Tetrahedron, 2001 , vol. 57, # 9 p. 1749 - 1755

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Citation Number: 9

Abstract

The synthesis of MEN11420, a potent tachykinin receptor antagonist, has been achieved. The bicyclic glycosylated structure of MEN11420 was constructed via intramolecular double cyclization using CIP-mediated activation. The head to tail cyclization of the linear precursor, which contained an α-amino acid at its C-terminus, proceeded so rapidly that no serious racemization was apparent at the activated carboxyl function. The desired product was ...