90380-02-2Relevant academic research and scientific papers
USE OF ALUMINA FOR ELIMINATION OF SULFINIC ACID FROM β-ARYL- AND β-ALKYLSULFONYL CARBONYL COMPOUNDS.
Vidal, Joelle,Huet, Francois
, p. 3733 - 3736 (1986)
Title compounds give α-unsaturated carbonyl compounds by treatment with basic alumina in dichloromethane or diethylether. α-Enones are thus obtained in high yield at room temperature.
SYNTHESES OF NITRILE AND METHYL ESTER CORRESPONDING TO (dl)-SARKOMYCIN AND OF RELATED COMPOUNDS.
Froissant, Jacques,Vidal, Joeelle,Guibe-Jampel, Eryka,Huet, Francois
, p. 317 - 322 (2007/10/02)
Nitrile 6a and ester 12 corresponding to (dl)-sarkomycin, 6- and 7-membered rings analogue nitriles 6b, 6c, and 3-methyl substituted nitrile 6d were prepared.Conjugate addition of cyanotrimethyl silane to cyclic α-enones gave 3-trimethylsiloxy 2-cycloalkene carbonitriles.Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to α-methylene carbonyl compounds.Obtention of the ester 12 involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, esterification, oxidation and elimination of sulfinic acid.
Regiospecific Synthesis of Sarkomycin and Some Analogues
Marx, John N.,Minaskanian, Gevork
, p. 3306 - 3310 (2007/10/02)
The first regiospecific total synthesis of the anticancer compound sarkomycin (1) is described.The starting material is 2-(carbomethoxycyclopent-2-enone (4), a useful precursor for cyclopentanoid natural products.The cyano derivative 5, the amide derivative 6, and the keto lactone 9 were also synthetized.The latter may be considered as a "cyclized" form of sarkomycin and was shown to open slowly to the natural product upon treament with dilute acid.
