SPIROKETAL EQUILIBRATION - INTERCONVERSION OF 1,6-DIOXASPIRO[4.4]NONANES AND 1,6-DIOXASPIRO[4.5]DECANES - IMPLICATIONS FOR THE SYNTHESIS OFCEPHALOSTATIN

Authors
JEONG JU FUCHS PL
Citation
Ju. Jeong et Pl. Fuchs, SPIROKETAL EQUILIBRATION - INTERCONVERSION OF 1,6-DIOXASPIRO[4.4]NONANES AND 1,6-DIOXASPIRO[4.5]DECANES - IMPLICATIONS FOR THE SYNTHESIS OFCEPHALOSTATIN, Tetrahedron letters, 35(30), 1994, pp. 5385-5388
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
30
Year of publication
1994
Pages
5385 - 5388
Database
ISI
SICI code
0040-4039(1994)35:30<5385:SE-IO1>2.0.ZU;2-P
Abstract
Acid-catalyzed equilibration of spiroketals 55H beta beta and 55H alph a beta involves a two stage process whereby the 1,6-dioxaspiro[4.4]non anes can be equilibrated under mild conditions to a pair of 1,6-dioxas piro[4.5]decanes with preservation of the adjacent C-20 methyl stereoc enter. Under more forcing conditions, both centers can be equilibrated in a reaction involving vinyl etheter intermediate 10H.