Work

Isolation, Identification, and Total Synthesis of Pyranoquinolinone Alkaloids from Conchocarpus mastigophorus Kallunki (Rutaceae)

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide In this study, the phytochemical profile of Conchocarpus mastigophorus was investigated, leading to the isolation of four pyranoquinolinone alkaloids, including huajiaosimuline ( 1 ) and three new compounds: 3′-acetoxy-4′-hydroxyzanthosimuline ( 2 ), epoxyzanthosimuline ( 3 ), and mastigophorine ( 4 ). All new compounds possess two chiral centers and exist as a 1:1 mixture of epimers, differing in the configuration of a chiral center at the pyran ring. The absolute configurations of the epimers 2 and 3 were determined by data comparison with identical synthetic compounds, revealing mixtures of (2 S,3' R ) - and (2 R,3' R )-configured epimers in both cases. By employing Sharpless asymmetric dihydroxylation and Shi epoxidation as key stereoselective steps, stereocontrol at C3 was achieved in the synthesis of compounds 2 and 3, respectively. Our synthesis approach provided 3 'R - and 3 'S -configured 2 in three steps (41–46% overall yield, 95% dr) and 3 'R -configured 3 in 2 steps (61% overall yield, 90% dr) from 4-hydroxy-1-methyl-2(1 H )-quinolinone and citral.

Source: Journal of Natural Products

DOI: 10.1021/acs.jnatprod.5c01326

Authors: Anderson R. Santos, Vanderlúcia F. de Paula, Amanda S. de Miranda, Júnio G. Silva, Luiz C. A. Barbosa

Institutions: Universidade Federal de Minas Gerais, Southwest Bahia State University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Conselho Nacional de Desenvolvimento Científico e Tecnológico