Analogues of the 2-carboxyl-6-hydroxyoctahydroindole (CHOI) unit from diverging Pd-catalyzed allylations: Selectivity as a function of the double bond position. Issue 44 (1st November 2017)

• Record Type: Journal Article
• Authors: Mao, Zhongyi; Martini, Elisabetta; Prestat, Guillaume; Oble, Julie; Huang, Pei-Qiang; Poli, Giovanni
• Is Part Of: Tetrahedron letters. Volume 58:Issue 44(2017)
• Page Start: 4174
• Page End: 4178
• Publication Date: 2017-11-01
• Subjects: Palladium catalysis -- CHOI core -- Allylic substitution -- Domino reaction -- Stereoselective synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.09.046
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: New analogues of the 2-carboxyl-6-hydroxyoctahydroindole (CHOI) building block. Key bicyclic lactams synthesized by diverging Pd-catalyzed allylations. Selectivity of introducing 1C unity as a function of the double bond position. Stereoselective epoxidation and dihydroxylation of 2-methoxycarbonyl hexahydroindoles. Abstract: 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.