Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides
作者:Bogdan Barnych、Jean-Michel Vatèle
DOI:10.1016/j.tet.2012.03.024
日期:2012.5
Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of beta-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclization-hydroperoxidation sequence. (C) 2012 Elsevier Ltd. All rights reserved.
610. The preparation of some cytotoxic epoxides
作者:James L. Everett、George A. R. Kon
DOI:10.1039/jr9500003131
日期:——
Efficient Synthesis of Medium-Sized Cyclic Ether Diamines
作者:Sang Hyup Lee、Harold Kohn
DOI:10.1021/jo0108663
日期:2002.3.1
Przybytek, Chemische Berichte, 1887, vol. 20, p. 3242