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Updated: Jun 16, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A
Santiago Díaz-Oltra1, César A Angulo-Pachón, Juan Murga
1Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, E-12071 Castellón, Spain.
Abstract:
A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate cyclic hemiacetal was one key feature of the synthesis. The macrocyclic lactone ring was created by means of a ring-closing metathesis (RCM), whereby the new C=C bond displayed exclusively the undesired Z configuration. Conversion to the required E configuration was achieved via photochemical isomerization.
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