Synthesis 2004(4): 558-567  
DOI: 10.1055/s-2004-815987
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Diels-Alder Approach for the Synthesis of Tetralin-Based α-Amino Acid Derivatives and their Modification by the Suzuki-Miyaura Cross-Coupling Reaction

Sambasivarao Kotha*, Arun Kumar Ghosh
Department of Chemistry, Indian Institute of Technology-Bombay, Mumbai, 400 076, India
Fax: +91(22)5723480; e-Mail: srk@chem.iitb.ac.in;
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Publikationsverlauf

Received 13 October 2003
Publikationsdatum:
26. Februar 2004 (online)

Abstract

Tetralin-based α-amino acid (AAA) is a constrained analogue of phenylalanine (Phe) and is used extensively in the design and synthesis of a variety of bioactive peptides. Due to the nonavailability of simple synthetic methods to deliver complex cyclic AAAs, only simplest members of this class have been used in the peptide area. In this regard, we have developed a new method to prepare various highly functionalized tetralin-based unusual AAA derivatives 22, 37-43 by trapping o-xylylene (or o-quino­dimethane) intermediate with methyl 2-acetamidoacrylate (12). In addition, we have also modified the diidotetralin derivative 40 by the Suzuki-Miyaura cross-coupling reaction.