TITLE

Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)-γ-Pelargonolactone

AUTHOR(S)
Valeev, F. A.; Gorobets, E. V.; Tsypysheva, I. P.; Singizova, G. Sh.; Kalimullina, L. Kh.; Safarov, M. G.; Shitikova, O. V.; Miftakhov, M. S.
PUB. DATE
November 2003
SOURCE
Chemistry of Natural Compounds;Nov/Dec2003, Vol. 39 Issue 6, p563
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Regiospecific C55 -halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C6 - substitution product. A stereoselective synthetic scheme for (+)-γ-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.
ACCESSION #
16935834

 

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