Use of silyloxydienes in synthesis. Total syntheses of the sesquiterpene (.+-.)-seychellene

ME Jung, CA McCombs, Y Takeda…

Index: Jung,M.E.; Mccombs,C.A.; Takeda,Y. Journal of the American Chemical Society, 1981 , vol. 103, p. 6677

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Citation Number: 57

Abstract

Abstract: 2-Silyloxy-1, 3-dienes, eg, 3, can be prepared from the corresponding enones and undergo facile Diels-Alder cycloaddition with typical dienophiles. The cyclic enol silyl ethers thus produced, eg, 5, can be readily converted into several functionalized ketone derivatives, eg, 7. By starting with 2, 3-dimethylcyclohex-2-enone (12), one can produce rapidly, via the 2-silyloxydiene 13, bicyclo [2.2. 2] octane systems in which the endo ...