(+)-3-Carene, an efficient chiral pool for the diastereoselective synthesis of b-lactams.

B M Bhawal, S N Joshi, D Krishnaswamy, A RAS Deshmukh

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


(+)-3-Carene; ketene; imines; Staudinger reaction; b-lactam.carbon bond formation.

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