REARRANGEMENT OF CYCLOBUTYL CARBINYL RADICALS - TOTAL SYNTHESIS OF THE SPIROVETIVANE PHYTOALEXIN (+ -)-LUBIMINOL/

Authors
CRIMMINS MT WANG Z MCKERLIE LA
Citation
Mt. Crimmins et al., REARRANGEMENT OF CYCLOBUTYL CARBINYL RADICALS - TOTAL SYNTHESIS OF THE SPIROVETIVANE PHYTOALEXIN (+ -)-LUBIMINOL/, Tetrahedron letters, 37(48), 1996, pp. 8703-8706
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
48
Year of publication
1996
Pages
8703 - 8706
Database
ISI
SICI code
0040-4039(1996)37:48<8703:ROCCR->2.0.ZU;2-L
Abstract
The total synthesis of the phytoalexin (+/-)-lubiminol 1 has been acco mplished. The synthesis relies on a conjugate addition-cyclization rea ction to prepare a photosubstrate for a stereoselective intramolecular photoaddition reaction. The photoadduct is transformed into the requi red spiro [5.4] decane through a radical fragmentation-rearrangement r eaction. Copyright (C) 1996 Published by Elsevier Science Ltd