THE TRANSFORMATION OF EPICANDICANDIOL INTO A GIBBERELLIN A(12) ISOMER

Authors
FRAGA BM HERNANDEZ MG ARRAEZ JD LUIS JG
Citation
Bm. Fraga et al., THE TRANSFORMATION OF EPICANDICANDIOL INTO A GIBBERELLIN A(12) ISOMER, Tetrahedron, 50(44), 1994, pp. 12643-12648
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
44
Year of publication
1994
Pages
12643 - 12648
Database
ISI
SICI code
0040-4020(1994)50:44<12643:TTOEIA>2.0.ZU;2-L
Abstract
Favorskii rearrangement of a chloro-enol-lactone (7), obtained in two steps from the diterpene epicandicandiol (1), afforded 9, which after hydrolysis led to the gibberellin A(12) isomer 10 The stereochemistry of the affected centres has been established as 5 alpha-K, 6 beta-H re vising the previously assigned 5 beta-H, 6 alpha-H. The structures of minor products obtained in the autoxidation of 7-oxo-ent-kaur-16-en-18 -methyl ester and in the reduction of 7-oxo-ent-kaur-5,16-dien-18-->6- olide have also been established.