Work

Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine

Year: 2019

Type: article

Abstract: Enantioselective syntheses of hexacyclic aspidoalbidine alkaloids (+)-fendleridine (2) and (+)-acetylaspidoalbidine (3) are described. These syntheses feature an asymmetric decarboxylative allylation and photocyclization of a highly substituted enaminone. Also, the synthesis highlights the formation of a C19-hemiaminal ether via a reduction/condensation/intramolecular cyclization cascade with the C21-alcohol. The present synthesis provides convenient access to the aspidoalbidine hexacyclic alkaloid family in an efficient manner.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.9b00145

Authors: Arun K. Ghosh, Joshua R. Born, Luke A. Kassekert

Institution: Purdue University West Lafayette

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Purdue University, National Institutes of Health, National Institute of General Medical Sciences

Awards: Mechanisms of the spliceosome protein SF3B1 and inhibitors, G618645967