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Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 681-685

N,O-Heterocycles as synthetic intermediates

Roderick W. Bates, Jutatip Boonsombat, Yongna Lu, Joseph A. Nemeth, Kanicha Sa-Ei, Ping Song, Melody Peiling Cai, Philippa B. Cranwell and SusAnn Winbush

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore

Abstract: Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.