Analogues of the 2-carboxyl-6-hydroxyoctahydroindole (CHOI) unit from diverging Pd-catalyzed allylations: Selectivity as a function of the double bond position

作者：Mao, Zhongyi; Martini, Elisabetta; Prestat, Guillaume; Oble, Julie^*; Huang, Pei-Qiang^*; Poli, Giovanni^*

来源：Tetrahedron Letters, 2017, 58(44): 4174-4178.

DOI：10.1016/j.tetlet.2017.09.046

• Palladium catalysis
• CHOI core
• Allylic substitution
• Domino reaction
• Stereoselective synthesis

Pd-catalyzed allylations of cyclic bis-allylic substrates, carried out either as two separate steps or in a pseudo-domino fashion, can generate 2-carboxyl-hexahydroindoles bearing an unsaturation in different positions. Sequential homologation, and epoxidation or syn-dihydroxylation steps were investigated to access analogues of the bicyclic 2-carboxyl-6-hydroxyoctahydroindole motif of aeruginosins, a family of peptides displaying serine protease inhibitor activity.

• 出版日期2017-11-1
• 单位厦门大学