Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol

Date

2004-02-09

Author

GÜLTEKİN, M SERDAR
Celik, M
TURKUT, ENGİN
Tanyeli, Cihangir
BALCİ, METİN

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

190
views

0
downloads

Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/48229

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2003.11.037

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Insertion of Fischer Carbene Complexes into the Carbon-Carbon Bond of 1,2-Diphenylcyclopropenone: Formation of Cyclobutenones and o- and p-Methoxyphenol Derivatives Zora, Metin (American Chemical Society (ACS), 1994-08-01) Thereactionbetween1,2-diphenylcyclopro-penoneandFischercarbenecomplexeshasbeeninves-tigated.Thereactionproducedamixtureofdipheny-lacetyleneandcyclobutenones.Whena,ß-unsaturatedcarbenecomplexeswereemployed,benzannulationprod-uctsanddiphenylacetylenewereproduced.Amecha-nisminvolvingmetallacyclobutenoneformation,followedbyeithercarbeneinsertionandreductiveeliminationorfragmentationhasbeenproposed.Recently,wereportedthatcarbon—carbonbondin-sertionisthemajorreactionpathwaywhenFischercarbenecomplexesreactwith1,2-...
SYNTHESIS AND STEREOCHEMISTRY OF PENTACARBONYL(PHOSPHOLE)METAL(0) AND TETRACARBONYLBIS(PHOSPHOLE)METAL(0) COMPLEXES OF 6B ELEMENTS OZER, Z; Özkar, Saim (Informa UK Limited, 1992-01-01) Pentacarbonylphospholemetal(0) and cis-tetracarbonylbis(phosphole)metal(0) complexes were synthesized from the thermal reaction of M(CO)5(THF) and M(CO)4(COD) (M: Cr, Mo, W) with corresponding phosphole (1-phenyl-3,4-dimethylphosphole, 1-phenyl-3-methylphosphole, and 1-phenylphosphole). These complexes were isolated as orange crystals by column chromatography on silicagel at 253 K and crystallization from n-hexane at 223 K and characterized by means of IR and NMR (H-1, C-13, and P-31). Spectroscopic data sh...
Corrigendum to “Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (−)- and (+)-proto-quercitol” [Tetrahedron: Asymmetry 15 (2004) 453] Gültekin, M.Serdar; Çelik, Murat; Turkut, Engin; Tanyeli, Cihangir; Balci, Metin (Elsevier BV, 2004-6) Photooxygenation of cyclohexa-1,4-diene affordedanti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydro-peroxy endoperoxide was reduced with dimethylsulfide–titanium tetraisopropoxide to produce (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplishedwithCandida cylindracealipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: Thecleavage of th...
Synthesis, characterization, and electrochemistry of tetracarbonyl(6-ferrocenyl-2,2 '-bipyridine)tungsten(0) Edinc, Pelin; Oenal, Ahmet M.; Özkar, Saim (Elsevier BV, 2007-04-15) 6-Ferrocenyl-2,2'-bipyridine (fcbpy) was prepared by the reaction of lithiated ferrocene with bipyridine and employed as a bidentate ligand for the formation of tetracarbonyl(6-ferrocenyl-2,2'-bipyridine)tungsten(0). The labile complex pentacarbonyl[eta(2)-bis(trimethylsilyl)ethyne]tungsten(0) reacts with fcbpy in CH2Cl2 to yield the disubstitution product, W(CO)(4)(fcbpy), which was isolated as analytically pure substance and characterized by elemental analysis, IR, UV-Vis, MS, H-1 and C-13 NMR spectroscop...
Selective recognition of anionic cell membranes using targeted liposomes coated with zinc(II)-bis(dipicolylamine) affinity units Türkyılmaz, Serhan; Palumbo, Rachael; Smith, Bradley D. (Royal Society of Chemistry (RSC), 2014-08-14) Zinc(II)-bis(dipicolylamine) (Zn(2)BDPA) coated liposomes are shown to have high recognition selectivity towards vesicle and cell membranes with anionic surfaces. Robust synthetic methods were developed to produce Zn(2)BDPA-PEG-lipid conjugates with varying PEG linker chain length. One conjugate (Zn(2)BDPA-PEG(2000)-DSPE) was used in liposome formulations doped with the Lipophilic near-infrared fluorophore DiR. Fluorescence cell microscopy studies demonstrated that the multivalent Liposomes selectively and ...

Citation Formats

M. S. GÜLTEKİN, M. Celik, E. TURKUT, C. Tanyeli, and M. BALCİ, “Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol,” TETRAHEDRON-ASYMMETRY, pp. 453–456, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48229.