719. The structure of alphitonin

Journal of the Chemical Society (Resumed)
1960.0

Abstract

Reduction of alphitonin pentamethyl ether with sodium in liquid ammonia removes a methoxyl group and gives the benzylcoumaranone (I) with potassamide in ammonia; this product affords the chalcone (11) but the alphitonin ether affords the amide (VI). Alphitonin therefore has the structure (V; R = H), a deduction confirmed by the synthesis of the ether (V; R = Me). The wood of Alphitonia excelsa also contains the triterpene emmolic acid.

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