Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 681-685
doi:10.1351/pac200880040681
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.
Keywords: cyclization; hydroxylamines; isoxazolidines; monomorine; Sakurai conditions; sedamine; tetrahydrooxazines.
*Paper based on a presentation at the 21st International Congress for Heterocyclic Chemistry (ICHC 21), 15-20 July 2007, Sydney, Australia. Other presentations are published in this issue, pp. 669-805.
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