Helvetica chimica acta

Short Syntheses of (±)??Grandisol and (±) Lineatin via, a common Intermediate

I Aljancic??Solaja, M Rey, AS Dreiding

Index: Aljancic-Solaja, Ivana; Rey, Max; Dreiding, Andre S. Helvetica Chimica Acta, 1987 , vol. 70, p. 1302 - 1306

Full Text: HTML

Citation Number: 12

Abstract

Abstract 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 ...