双环叔α-氨基酸的合成。

Synthesis of bicyclic tertiary alpha-amino acids.

作者信息

Strachan Jon-Paul, Whitaker Regina C, Miller Craig H, Bhatti Balwinder S

机构信息

Targacept, Inc., Winston-Salem, North Carolina 27101-4165, USA.

出版信息

J Org Chem. 2006 Dec 22;71(26):9909-11. doi: 10.1021/jo061977a.

DOI:10.1021/jo061977a

PMID:17168622

Abstract

Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.

摘要

新型双环α-氨基酸，外型和内型-1-氮杂双环[2.2.1]庚烷-2-羧酸、1-氮杂双环[2.2.1]庚烷-7-羧酸和1-氮杂双环[3.2.2]壬烷-2-羧酸已被轻松合成，用于生成神经元烟碱受体配体。用环状醚亲电试剂对甘氨酸衍生的席夫碱或硝基乙酸酯进行烷基化，然后在NH4OH中进行酸诱导的开环和环化，从而制备出大量的三种叔双环α-氨基酸。