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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Optimized Asymmetric Synthesis of Umuravumbolide
Marina Pérez-Palau1, Eduard Balaguer-Garcia1, Pedro Romea1
1Departament de Química Inorgànica i Orgànica, Secció de Química Orgànica, and Institut de Biomedicina de la Universitat de Barcelona (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
Abstract:
Herein, the asymmetric synthesis of umuravumbolide (1) is described. The new approach features highly stereoselective transformations (dr ≥ 95:5) to install both stereocenters and the Z olefin, which involve a new radical alkylation, an Ando olefination, and a Krische allylation on a Z allylic alcohol, not reported before. The application of such successful reactions, together with the limited use of protecting groups and concession steps, makes it possible to complete the synthesis in 10 steps, resulting in a 39% overall yield from chiral N-acyl oxazolidinone 2.
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