Add time:08/01/2019         Source:sciencedirect.com

A stereospecific synthesis of aklavinone (2) in 16 steps from 5-methoxy- 1-tetralone with an overall yield of 6.5% is described. Regiospecific control in forming the BCD-ring chromophore was accomplished by coupling of a preformed bicyclic AB-ring aldehyde (29) with a nucleophilic D-ring carboxamide (3), with stepwise bond formation as illustrated in equation 2. The coupled product was subsequently transformed into (±)-aklavinone. An enantioselective synthesis of aklavinone was achieved in 53%. e.e. using the procedure of Sharpless for the asymmetric epoxidation of allylic alcohol 2413

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