STEREOCHEMISTRY OF 4,5-DIHYDROXY-ALPHA-SANTONIN AND STRUCTURE OF A NEW SANTONIN OXIDATION-PRODUCT

Authors
PAKNIKAR SK MALIK BL BATES RB CALDERA S WIJAYARATNE TV
Citation
Sk. Paknikar et al., STEREOCHEMISTRY OF 4,5-DIHYDROXY-ALPHA-SANTONIN AND STRUCTURE OF A NEW SANTONIN OXIDATION-PRODUCT, Tetrahedron letters, 35(44), 1994, pp. 8117-8118
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
44
Year of publication
1994
Pages
8117 - 8118
Database
ISI
SICI code
0040-4039(1994)35:44<8117:SO4ASO>2.0.ZU;2-E
Abstract
The diol, mp 220 degrees C, obtained by KMnO4 oxidation of alpha-santo nin is shown by an nOe study to be 4 beta,5 beta- rather than 4 alpha, 5 alpha-dihydroxy-alpha-santonin. On further oxidation with Pb(OAc)(4) , it unexpectedly gives a new ketolactone, mp 268 degrees C, which is also obtained as a KMnO4 oxidation product of alpha-santonin.