Helvetica Chimica Acta p. 1302 - 1306 (1987)
Update date:2022-08-17
Topics:
Aljancic-Solaja, Ivana
Rey, Max
Dreiding, Andre S.
A 6-step synthesis of (+/-)-grandisol (1) is presented, which involves dichloroketene addition to 3-methyl-3-butenyl acetate (4), reductive dechlorination of the adduct 6 to the ketone 7 and saponification to 8, aldolization of 7 or 8 with acetone and cyclization to the bicyclic ketone 9, Wolff-Kishner reduction to 14, and finally ring opening to 1.Since 9 is a known intermediate of the synthesis of (+/-)-lineatin (2), the latter can now be obtained in 6 steps.
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