Synthetic studies on morellin. Part4: Synthesis of 2, 2- dimethyl - 12 - [ 3- methylbut - 2 - enyl ] - 2H, 6H-pyrano [3, 2- b] xanthen -6- one.

G R S SubbaRao, Sadagopan Raghavan

Abstract


A new synthesis of 2 , 2 - dimethyl - 12 - [ 3 - methylbut - 2 - enyl ] - 2H , 6H - pyrano [ 3 , 2 - b ] xanthen - 6 - one (7) is described from 1 , 3 - dihydroxyxanthone and involved the preparation of a linear dihydropyranoxanthone (26) , its conversion into the pyranoxanthone (14) and its prenylated derivative (31) followed by a Claisen rearragement leading to the target substrate (7).

Keywords


Morellin; synthetic studies; pyrano[3;2-b]xanthene; Claisen rearrangement.

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