STEREOCONTROLLED SYNTHESIS OF SPIROSUCCINIMIDE DERIVATIVE OF (-HYDANTOCIDIN())

Authors
SANO H MIO S TSUKAGUCHI N SUGAI S
Citation
H. Sano et al., STEREOCONTROLLED SYNTHESIS OF SPIROSUCCINIMIDE DERIVATIVE OF (-HYDANTOCIDIN()), Tetrahedron, 51(5), 1995, pp. 1387-1394
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
5
Year of publication
1995
Pages
1387 - 1394
Database
ISI
SICI code
0040-4020(1995)51:5<1387:SSOSDO>2.0.ZU;2-6
Abstract
Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the prot ected D-psicose 3 with allyltrimethlsilane in dichloromethane, which p roceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.