An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

Baran, A
Secen, H
Balcı, Metin
gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aalpha,5alpha,7aalpha)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole. cis-Hydroxylation of the benzodioxole followed by acetylation with AcCl gave 5-O-methyl-gala-quercitol tetraacetate from which gala-quercitol was obtained by hydrolysis and demethylation with aq HBr (47%).


Application of ferrocenyl substituted aziridinylmethanols (FAM) as chiral ligands in enantioselective conjugate addition of diethylzinc to enones
İŞLEYEN, Alper; Doğan, Özdemir (Elsevier BV, 2007-03-30)
Easily available ferrocenyl substituted aziridinylmethanol FAM-4a complexes with nickel and catalyzes the enantioselective diethylzinc addition to various enones with enantiomeric excesses reaching 80%. The ligand can be recovered and used without losing its activity. The sense of induction was found to be dependent on the configuration of the aziridine ring.
Uncatalyzed addition of TMSCN to acylphosphonates
Demir, Ayhan Sıtkı; Reis, Omer; Kayalar, Metin; Eymur, Serkan; Reis, Barbaros (Georg Thieme Verlag KG, 2006-12-01)
The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethyl-silyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.
Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity
Ayan, Seylan; Doğan, Özdemir; Ivantcova, Polina M.; Datsuk, Nikita G.; Shulga, Dmitry A.; Chupakhin, Vladimir I.; Zabolotnev, Dmitry V.; Kudryavtsev, Konstantin V. (Elsevier BV, 2013-07-31)
The (2R,4R,5S)- and (2S,4S,5R)-enantiomers of 4-(tert-butyl) 2-methyl 5-(4-bromophenyl)-pyrrolidine-2,4-dicarboxylate 3 were synthesized efficiently with an ee of >90% on a gram scale using a FAM-catalytic methodology. Subsequent modification afforded enantiopure N-((4-chlorophenyl)thio)acetyl pyrrolidine derivatives 4, which are potential thrombin inhibitors according to comprehensive molecular docking studies.
A facile synthesis of various butenolides
Tanyeli, Cihangir (Informa UK Limited, 2000-01-01)
The synthesis of alpha'-acyloxy-alpha,beta-unsaturated cyclic ketones from the corresponding alpha,beta-unsaturated cyclic ketones by using manganese (III) acetate in combination with 2-chloropropionic acid followed by subsequent Arbuzov and intramolecular Horner-Emmons cyclization reactions provided a convenient synthetic pathway to various butenolides 4a-d.
An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone
Demir, Ayhan Sıtkı; Sesenoglu, O; Gercek-Arkin, Z (Elsevier BV, 2001-09-13)
The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into (E)- and (Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91-93% yields.
Citation Formats
A. Baran, H. Secen, and M. Balcı, “An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene,” SYNTHESIS-STUTTGART, pp. 1500–1502, 2003, Accessed: 00, 2020. [Online]. Available: