Total Synthesis of 4--Bengamide E

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2024 Apr 27

PMID 38675534

Authors

Gabriella Vitali Forconesi

Andrea Basso

Luca Banfi

Davide Gugliotta

Chiara Lambruschini

Marta Nola

Renata Riva

Valeria Rocca

Lisa Moni

Affiliations

Soon will be listed here.

Abstract

Bengamide E is a bioactive natural product that was isolated from Jaspidae sponges by Crews and co-workers in 1989. It displays a wide range of biological activities, including antitumor, antibiotic, and anthelmintic properties. With the aim of investigating the structural feature essential for their activity, several total syntheses of Bengamide E and its analogues have been reported in the literature. Nevertheless, no synthesis of the stereoisomer with modification of its configuration at C-4 carbon has been reported so far. Here, we report the first total synthesis of the 4--Bengamide E. Key reactions in the synthesis include a chemoenzimatic desymmetrization of biobased starting materials and a diastereoselective Passerini reaction using a chiral, enantiomerically pure aldehyde, and a lysine-derived novel isocyanide.

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