Synthesis of functionalized bicyclo [3.2. 1] octa-2, 6-dienes by thermal rearrangement of substituted 6-exo-(1-alkenyl) bicyclo [3.1. 0] hex-2-ene systems

E Piers, GL Jung, EH Ruediger

Index: Piers, Edward; Jung, Grace L.; Ruediger, Edward H. Canadian Journal of Chemistry, 1987 , vol. 65, p. 670 - 682

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Citation Number: 40

Abstract

Thermolysis of each of the enol silyl ethers 31-35 affords, cleanly and efficiently, the bicyclo [3.2. 1] octadienes 36-40, respectively. Similarly, thermal rearrangement of the enol silyl ether 50 provides the diene 51. Hydrolysis of 36, 37, and 39, and decarbomethoxylation of the resultant keto esters 41, 42, and 44, gives the ketones 46-48, respectively. The ketone 46 is also obtained by acid hydrolysis of 51. Conversion of 6-methyl-1-hepten-4-yn-3-ol ( ...