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Stereoselective Bromination−Suzuki Cross-Coupling of Dehydroamino Acids To Form Novel Reverse-Turn Peptidomimetics: Substituted Unsaturated and Saturated Indolizidinone Amino Acids
journal contribution
posted on 2002-10-24, 00:00 authored by Junyi Zhang, Chiyi Xiong, Wei Wang, Jinfa Ying, Victor J. HrubyA general and efficient methodology has been developed to prepare the C4-substituted dipeptide reverse-turn mimetics unsaturated (9a, 10a)
and saturated (11a) azabicyclo[4.3.0] alkane amino acid derivatives. The side chain was introduced by bromination of dehydroamino acid
intermediates followed by Suzuki coupling. Hydrogenation of the bicyclic dehydroamino acid 9a afforded saturated bicyclic lactam 11a. This
approach can be further explored for the synthesis of a variety of such β-turn mimetics with aryl and alkyl side chain functionalities.
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