Synthesis of osajaxanthone

Jain, A. C. ; Khanna, V. K. ; Seshadri, T. R. (1969) Synthesis of osajaxanthone Tetrahedron, 25 (14). pp. 2787-2793. ISSN 0040-4020

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Prenylation of 1,3-dihydroxy-7-methoxyxanthone (1) with prenyl bromide and methanolic methoxide yielded a mixture of 2-C-prenyl derivative (4a), 2,4-di-C-prenyl derivative (2) and 3-O-prenyl derivative (3). 2-C-Prenyl derivative (4a) with HI gave a mixture of dihydro-osajaxanthone (8) and its angular isomer (9). The acetate of the former with excess of NBS gave a dibromo derivative which on dehydrobromination with pyridine and deacetylation with alcoholic potash formed 4'-bromo-osajaxanthone (11) in good yield. Refluxing with zinc and glacial acetic acid afforded osajaxanthone (13) identical with a natural sample.

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