Acid-promoted Fries rearrangements of benzannulated lactones

Authors
Cambie, RC Mitchell, LH Rutledge, PS
Citation
Rc. Cambie et al., Acid-promoted Fries rearrangements of benzannulated lactones, AUST J CHEM, 51(12), 1998, pp. 1167-1174
Citations number
29
Categorie Soggetti
Chemistry
Journal title
AUSTRALIAN JOURNAL OF CHEMISTRY
ISSN journal
00049425 → ACNP
Volume
51
Issue
12
Year of publication
1998
Pages
1167 - 1174
Database
ISI
SICI code
0004-9425(1998)51:12<1167:AFROBL>2.0.ZU;2-1
Abstract
The scope of acid-promoted Fries rearrangements of benzannulated lactones h as been examined. The reaction is applicable to seven-membered lactones pos sessing a sufficiently activated aromatic ring but not to six-membered lact ones, and it proceeds in higher yield for diterpenoid lactones than for low er molecular weight lactones. The structures of the 2,6-methano-bridged ben zoxocin side products (23), (24), and (25) from rearrangement of the diterp enoid lactone (11) have been assigned.