PHOTOCHEMICAL REARRANGEMENTS OF HIGHLY FUNCTIONALIZED LONGIPINENE DERIVATIVES

Authors
JOSEPHNATHAN P MELENDEZRODRIGUEZ M CERDAGARCIAROJAS CM CATALAN CAN
Citation
P. Josephnathan et al., PHOTOCHEMICAL REARRANGEMENTS OF HIGHLY FUNCTIONALIZED LONGIPINENE DERIVATIVES, Tetrahedron letters, 37(45), 1996, pp. 8093-8096
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
45
Year of publication
1996
Pages
8093 - 8096
Database
ISI
SICI code
0040-4039(1996)37:45<8093:PROHFL>2.0.ZU;2-X
Abstract
Ultraviolet irradiation of 7 beta,9 alpha-diacetyloxylongipin-2-en-1-o ne (3) affords the vulgarone A derivative 5 and compound 7 which posse sses a novel tricyclic sesquiterpene skeleton named pingilonane. The p hotorearrangements of 3 occur via [1,3] sigmatropic shifts of the C-4- C-10 or of the C-4-C-5 bond, respectively. Similarly, irradiation of 7 beta,8 alpha,9 alpha-triacetyloxylongipin-2-en-1-one (4) affords 6 an d 8. Some biogenetic implications of these transformations are discuss ed. Copyright (C) 1996 Elsevier Science Ltd