Total syntheses of hyacinthacine A(2) and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone

Practical syntheses of nitrone 8 by two different approaches from sugars are reported. Its use as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A(2) (3) and 7-deoxycasuarine (20) by simple transformations of a common isoxazolidine adduct. (C) 2003 Elsevier Science Ltd. All rights reserved.