Work

Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels–Alder Cycloaddition**

Year: 2022

Type: article

Abstract: We report the first total synthesis of the monoterpene indole alkaloids ophiorrhine A via a late stage bioinspired intramolecular Diels-Alder cycloaddition to form the intricate bridged and spirannic polycyclic system. Several strategies were investigated to construct the indolopyridone moiety of ophiorrhiside E, the postulated biosynthetic precursor of ophiorrhine A. Eventually, the Friedel-Crafts-type coupling of N-methyl indolyl-acetamide with a secologanin-derived acid chloride delivered ophiorrhine G. Cyclodehydration of a protected form of the latter was followed by the desired spontaneous intramolecular Diels-Alder cycloaddition of protected ophiorrhiside E leading to ophiorrhine A.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202209135

Authors: Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent

Institutions: Centre National de la Recherche Scientifique, Université Paris-Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,100

Funders: University of Texas Southwestern Medical Center, China Scholarship Council, Centre National de la Recherche Scientifique, Université Paris-Saclay