1, 2-Addition of TMS-CF3 and TMS-CN tosterically crowded 2, 2, 4, 4-tetramethyl-1, 3-cyclobutanedione and related studies

JORG STEPHAN BRUNCH, ANNETTE KOCH, GRZEGORZ MLOSTON, STEFAN LEHNHOFF, PAUL MARGARETHA, G K SURYA PRAKASH, GOLAM RASUL, ROBERT BAU, GEORGE A OLAH, Donald P, Katherine B

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).

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