159276-58-1Relevant articles and documents
Concise Synthesis of 1,3-Diacetoxy-2-[2′-(2′′,4′′-difluorophenyl)prop-2′-en-1′-yl]propane: An Intermediate for Posaconazole
Chen, Yunxiang,Huang, Yangwei,Zhao, Xueqing,Li, Zhongming
, p. 744 - 750 (2015)
A concise process of 1,3-diacetoxy-2-[2′-(2″,4″-difluorophenyl)prop-2′-en-1′-yl]propane has been developed. Diethyl malonate was C-alkylated with 2,3-dichloropropene and then the ester groups were reduced by LiAlH4 followed by acylation to provide 2-(2′-chloroprop-2′-en-1′-yl)-1,3-diacetoxypropane. The chloropropene was finally coupled with 2,4-difluorophenylmagnesium bromide and catalyzed by Fe(acac)3 to afford the title compound in good total yield. GRAPHICAL ABSTRACT.
HIGHLY STEREOSELECTIVE ACCESS TO NOVEL 2,2,4-TRISUBSTITUTED TETRAHYDROFURANS BY HALOCYCLIZATION: PRACTICAL CHEMOENZYMATIC SYNTHESIS OF SCH 51048, A BROAD-SPECTRUM ORALLY ACTIVE ANTIFUNGAL AGENT
Saksena, Anil K.,Girijavallabhan, Viyyoor M.,Lovey, Raymond G.,Pike, Russell E.,Wang, Haiyan,et al.
, p. 1787 - 1790 (2007/10/02)
A convenient synthesis of (-)-(2R)-cis-tosylate 2 is reported via stereoselective 5-exo iodocyclization of the optically active 2,2-disubstituted olefin 9a.Enzymatic desymmetrization of the homoallylic diol 4 with Novo SP435 allowed optimal pro-(S) selectivity to provide the desired (-)-(S)-monoacetate 9a.Under the irreversible reaction conditions, the presence of a bulky aryl substituent on the 2,2-disubstituted olefin seems to determine stereochemical outcome of these halocyclizations.
