Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies.
The expedient and fully stereocontrolled synthesis of epothilones A and B are described. The routes described make extensive study of nitrile oxide cycloadditions as surrogates for aldol addition reactions and have led to the realization of a highly convergent synthesis based on the Kanemasa hydroxyl-directed nitrile oxide cycloaddition. As well, our synthetic efforts have led to the development of new reaction methodologies and served as the proving ground for several modern methods for asymmetric carbon-carbon bond formation.
Bode
J W
JW
Laboratorium für Organische Chemie, ETH-Zürich, Universitätstrasse 16, CH-8092 Zürich/Switzerland.
Carreira
E M
EM
D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis*
D000447:Aldehydes; D000970:Antineoplastic Agents; D034261:Epothilones; D004852:Epoxy Compounds; D013844:Thiazoles; D009569:Nitric Oxide; C093787:epothilone A; C116609:3-hydroxybutanal; C093788:epothilone B