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2005
Enantioselective syntheses
O 0031
Application of Chiral Cationic Catalysts to Several Classical Syntheses of RacemNatural Products Transforms Them into Highly Enantioselective Pathways.
11- 037 ic
— Chiral oxazaborolidinium cations (I) and (II) are applied to the Diels—Alder reaction step of eight classical racemic syntheses of natural products. Key intermediates of
these syntheses are thus obtained in optically pure form, e.g. (V) - leading to cortisone,
(VIII) - leading to (-)-dendrobine, (X) - leading to vitamin B12, (XIII) - leading to dendrobatid 251F and (XV) - leading to silphinene. — (HU, Q.-Y.; ZHOU, G.; COREY*,
E. J.; J. Am. Chem. Soc. 126 (2004) 42, 13708-13713; Dep. Chem. Chem. Biol.,
Harvard Univ., Cambridge, MA 02138, USA; Eng.) — Nuesgen
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