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Removal of 4 hydroxyl group in 4 hydroxy 3 methoxy coumarins synthesis of 3 methoxy angelicin and partial methyl ethers of 3 methoxy coumarins



Removal of 4 hydroxyl group in 4 hydroxy 3 methoxy coumarins synthesis of 3 methoxy angelicin and partial methyl ethers of 3 methoxy coumarins



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 16(7): 587-590



The 4-hydroxyl group in 4-hydroxy-3-methoxycoumarins was removed by reductive detosylation with Zn-HCl of the appropriate 4-tosyloxycoumarin. Using this method 3,7-dimethoxy- and 3,5,7-trimethoxy-coumarins were prepared. The method was also used for the preparation of partial methyl ethers, namely, 7-hydroxy-3-methoxy-(II), 7-hydroxy-3,5-dimethoxy and 5-hydroxy-3,7-dimethoxy-coumarins. These partial methyl ethers are useful intermediates for the synthesis of 3-methoxyfuranocoumarins. 3-Methoxyfurano[4',5':7,8]coumarin (XXII) (3-methoxyangelicin) was synthesized from II by allylation to 7-allyloxy-3-methoxycoumarin (XXIII). Claisen migration of XXIII gives 8-allyl-7-hydroxy-3-methoxycoumarin which on oxidation with OsO4-KIO4 and subsequent cyclization of the intermediate phenyl acetaldehyde furnishes XXII. [The antiveratrinic activity of 3-methoxycoumarins and their use for the treatment of certain forms of myotonia prompted development of a complete synthesis of 3-methoxycoumarins.].

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