Abstract
Obtusinin (1) has been synthesised by the reaction of 6-methoxy-7-(3′-methylbut-2′-enyloxy)-2H-1-benzopyran-2-one (3) with OsO4. Synthesis of 7-(3′-hydroxymethylbut-2′-enyloxy)-6-methoxy-2H-1-benzopyran-2-one (2) has been achieved by the regiospecific oxidation of3 with SeO2 followed by reduction of the formed aldehyde with KBH4.
Zusammenfassung
Obtusinin (1) wurde über 6-Methoxy-7-(3′-methylbut-2′-enyloxy)-2H-1-benzopyran-2-on (3) mit OsO4 synthetisiert. Die Darstellung von 7-(3′-Hydroxymethylbut-2′-enyloxy)-6-methoxy-2H-1-benzopyran-2-on (2) wurde mittels regioselektiver Oxidation von3 mit SeO2, gefolgt von Reduktion des gebildeten Aldehyds mit KBH4, bewerkstelligt.
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References
Matkarimov A. D.,Batirov E. K.,Malikov V. M.,Seitmuratov E., Khim. Prir. Soedin1980, 328.
Ibid.1980, 565.
Herz W., Bhat S. V., Santhanam P. S., Phytochemistry9, 891 (1970).
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Ahluwalia, V.K., Khanna, M. & Singh, R.P. Synthesis of obtusinin and 7-(3′-hydroxymethylbut-2′-enyloxy)-6-methoxy-2H-1-benzopyran-2-one. Monatsh Chem 113, 197–200 (1982). https://doi.org/10.1007/BF00799019
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DOI: https://doi.org/10.1007/BF00799019