A modular approach to polyketide building blocks: cycloadditions of nitrile oxides and homoallylic alcohols.
A general approach to the diastereoselective synthesis of Delta(2)-isoxazolines via magnesium-mediated, hydroxyl-directed diastereoselective nitrile oxide cycloadditions of homoallylic alcohols and monoprotected homoallylic diols is disclosed. A broad spectrum of aliphatic and aromatic nitrile oxides and a variety of homoallylic alcohols participate in the cycloaddition, thus expanding the scope of polyketide building blocks that can be accessed using this strategy.
Lohse-Fraefel
Nina
N
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI, Zürich, Switzerland.
Carreira
Erick M
EM
D000438:Alcohols / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007555:Isoxazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D001688:Biological Products; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides