Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure

…, B Arison, L Maechler, A Rosegay, PA Sprengeler…

Index: Hirschmann, Ralph; Yao, Wenqing; Arison, Byron; Maechler, Laurie; Rosegay, Avery; Sprengeler, Paul A.; Smith III, Amos B. Tetrahedron, 1998 , vol. 54, # 25 p. 7179 - 7202

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Citation Number: 10

Abstract

The discovery of somatostatin antagonists at one or more receptor subtypes remains an important goal. We therefore undertook the synthesis of the homodetic tricyclic peptide (1) hoping to cause conformational distortion and thereby achieve this biological goal. The synthetic strategy called for five dimensional orthogonal amino protection. The carboxyl and amino protecting groups were selected to assure the desired selective ring closures. The ...