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Synthesis 2011(18): 2945-2950  
DOI: 10.1055/s-0030-1260145
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Linearly and Angularly Fused Indane-Based Constrained α-Amino Acid Derivatives

Sambasivarao Kotha*, Nimita Gopal Krishna, Shilpi Misra, Priti Khedkar
Department of Chemistry, , Indian Institute of Technology-Bombay, Mumbai 400076, India
Fax: +91(22)25767152; e-Mail: srk@chem.iitb.ac.in;
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Publication History

Received 16 May 2011
Publication Date:
02 August 2011 (online)

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Abstract

The benzocyclobutene-based α-amino acid derivative, ethyl 5-acetamido-2,4,5,6-tetrahydro-1H-cyclobuta[f]indene-5-carboxylate is synthesized via coupling of a benzocyclobutene-derived dibromide with ethyl isocyanoacetate as the key step, followed by hydrolysis and subsequent acetylation. This methodology is generalized in order to prepare various linearly and angularly fused indane-based α-amino acid derivatives.

Key words

α-amino acids - [2+2+2] cycloaddition - indane-based α-amino acid - benzocyclobutene - ethyl isocyanoacetate - diversity-oriented approach