2570-90-3Relevant academic research and scientific papers
BIOACTIVE MARINE METABOLITES V. TWO NEW FURANOSESTERTERPENES, INHIBITORS OF CELL DIVISION OF THE FERTILIZED STARFISH EGGS, FROM THE MARINE SPONGE CACOSPONGIA SCALARIS
Fusetani, N.,Kato, Y.,Matsunaga, S.,Hashimoto, K.
, p. 4941 - 4942 (2007/10/02)
Two new furanosesterterpenes have been isolated from the marine sponge C. scalaris as inhibitors of the cell division of fertilized starfish eggs.
Electrooxidative Cleavage of Carbon-Carbon Linkages. 1. Preparation of Acylic Oxoalkanoates from 2-Hydroxy- and 2-Acetoxy-1-cycloalkanones and Cycloalkanone Enol Acetates
Torii, Sigeru,Inokuchi, Tsutomu,Oi, Ryu
, p. 47 - 52 (2007/10/02)
A methodology is described for the synthesis of acyclic oxoalkanoates 2 by electrooxidative cleavage of carbon-carbon linkages of 2-oxocycloalkan-1-ols 1 and cycloalkanone enol acetates 3.The electrolysis of 1 was carried out in a MeOH-LiClO4-(Pt) system at a constant applied voltage of 20 V by using a divided cell, giving 2 in 82-97 percent yields.On the other hand, 3 was electrolyzed in MeOH-AcOH (10:1)-LiClO4-(Pt) at 2-8 deg to give 2 in 72-79 percent yields.Electrolysis of 4-hydroxy-p-menth-8-ene afforded methyl (3R)-3,7-dimethyl-6-oxo-7-octenoate, a chiral synthetic block for the synthesis of (+)-rose oxide, in 84 percent yield.Similarly, the procedure could be applied to the preparation of methyl(+)-6-oxo-6,7-dihydrocitronellate from (+)-menthone enol acetate (74 percent) as well as 4-hydroxy-p-menthone (94 percent).Other lithium salts, i.e., LiBF4 and CF3CO2Li, can be used for the present purpose, but there are some difficulties in producing 2 with Et4NOTs and Et4NClO4.A plausible mechanism of the formation of 2 from 1 is also discussed.
