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Updated: Jun 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Polyketide building blocks via diastereoselective nitrile oxide cycloadditions with homoallylic alcohols and
Nina Lohse-Fraefel1, Erick M Carreira
1Laboratorium für Organische Chemie, ETH Zürich, HCI H335, 8093 Zürich, Switzerland.
Abstract:
A modular approach to Delta(2)-isoxazolines, latent aldol adducts and polyketide building blocks, is reported. The magnesium-mediated, hydroxyl-directed method allows for the diastereoselective access to a wide variety of masked beta-hydroxy ketones, starting from readily available aliphatic and aromatic oximes, homoallylic alcohols and monoprotected homoallylic diols. The utility of the prepared Delta(2)-isoxazolines as polyketide building blocks is demonstrated by their ready conversion into the corresponding beta-hydroxy ketones. The anti-diastereoselectivity of the reaction was established by derivatization, NOE studies and comparison of known compounds. A rationale for the observed diastereoselectivity is proposed.
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