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J Org Chem. 2008 Sep 5;73(17):6706-10. doi: 10.1021/jo801006a. Epub 2008 Jul 26.

Amino-zinc-ene-enolate cyclization: a short access to cis-3-substituted prolino-homotryptophane derivatives.

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  • 1UPMC Univ Paris 06, UMR 7613 and FR2769, Synthèse, Structure et Fonction de Molécules Bioactives, Fédération de Chimie Moléculaire, UPMC, 4, Place Jussieu, 75252, Paris Cedex 05, France.

Abstract

Proline chimeras are useful tools for medicinal chemistry and/or biological applications. The asymmetric synthesis of cis-3-substituted prolines can be easily achieved via amino-zinc-ene-enolate cyclization followed by transmetalation of the cyclic zinc intermediate for further functionalization. Syntheses of prolino-homotryptophane derivatives were achieved through Negishi cross-coupling of the zinc intermediate with indole rings. The use of Pd catalyst derived from Fu's [(t-Bu3)PH]-BF4 was required to avoid the undesired beta-hydride elimination. Optically pure and orthogonally protected compounds were obtained readily usable for peptide synthesis.

PMID:
18656982
[PubMed - indexed for MEDLINE]
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