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http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2586| Title: | Stereospecific synthesis of novel methyl-substituted mono- and di-methoxy conduritols |
| Authors: | Kaplan, Dilek Kelebekli, Latif Ordu Üniversitesi |
| Keywords: | Conduritol; Methyl-methoxy conduritol-B; Methyl-conduritol RING-CLOSING METATHESIS; (+)-PERICOSINE B; CHEMOENZYMATIC SYNTHESIS; MONOSUBSTITUTED BENZENES; SECONDARY METABOLITES; GENERAL PROCEDURE; CARBA-SUGARS; GABOSINE-G; DERIVATIVES; STREPTOMYCES |
| Issue Date: | 2017 |
| Publisher: | PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND |
| Abstract: | Methyl-monomethoxy conduritol-B and methyl-dimethoxy conduritol-B were synthesized starting from 2-methylbenzo-1,4-quinone. Bromination of 2-methylbenzo-1,4-quinone was followed by the reduction of the carbonyl groups with NaBH4 to give a dioldibromo compound. Methyl-dimethoxy conduritol-B was synthesized from the reaction of the dioldibromo compound with CH3ONa, followed by acetylation with Ac2O-pyridine to obtain methyl-dimethoxy diacetate. On the other hand, acetylation of the methyldioldibromo compound followed by reaction with LiOH gave a monoepoxide compound stereo selectively. The reaction of the epoxide with H+/Ac2O afforded the monobromo triacetate. Controlled reaction of monobromo-triacetate with CH3ONa in MeOH furnished the desired new methylmonomethoxy conduritol-B. The structures of all synthesized compounds were characterized by spectroscopic methods. (C) 2016 Elsevier Ltd. All rights reserved. |
| URI: | http://doi.org/10.1016/j.tet.2016.11.042 https://www.sciencedirect.com/science/article/pii/S0040402016311978?via%3Dihub http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2586 |
| Appears in Collections: | Kimya |
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