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Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0]decane skeleton.

ABSTRACT: An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C? or -C? side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.0²,?]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for beta-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

SUBMITTER: Breuning M

PROVIDER: S-EPMC2839531 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0]decane skeleton.

Breuning Matthias M Häuser Tobias T Mehler Christian C Däschlein Christian C Strohmann Carsten C Oechsner Andreas A Braunschweig Holger H

Beilstein journal of organic chemistry 20091221

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C₁ or -C₂ side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.0²,⁶]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for beta-turn-in ...[more]

PMID: 20300505

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