由γ-和δ-内酯断裂合成γ,δ-不饱和及δ,ε-不饱和α-氨基酸。

Synthesis of gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids from fragmentation of gamma- and delta-lactones.

作者信息

Tarver James E, Joullié Madeleine M

机构信息

Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

J Org Chem. 2004 Feb 6;69(3):815-20. doi: 10.1021/jo035401m.

DOI:10.1021/jo035401m

PMID:14750809

Abstract

A noncoded amino acid of cyclomarin A (1) was synthesized in a racemic fashion. The method employs a six-membered ring template to control the relative stereochemistry and introduction of the functional groups. Ultimately, Pd-catalyzed fragmentation of the lactone provided gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids. A Pd-catalyzed ring opening of a gamma-lactone is also reported.

摘要

以外消旋方式合成了环海葵毒素A（1）的一种非编码氨基酸。该方法采用六元环模板来控制相对立体化学和官能团的引入。最终，内酯的钯催化碎片化反应得到了γ,δ-不饱和和δ,ε-不饱和α-氨基酸。还报道了γ-内酯的钯催化开环反应。