Unexpected Stereochemistry in the
Lithium Salt Catalyzed Ring Expansion
of Nonracemic Oxaspiropentanes.
Formal Syntheses of
(−)-(4R,5R)-Muricatacin and the
Pheromone (R)-Japonilure
posted on 2003-07-12, 00:00authored byAngela M. Bernard, Angelo Frongia, Pier P. Piras, Francesco Secci
The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2,
depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the
acetogenin (−)-(4R,5R)-muricatacin and the pheromone (R)-japonilure.