Synthesis and absolute configuration of (-)-rothrockene, a non-head-to-tail monoterpene

MR Barbachyn, CR Johnson…

文献索引：Barbachyn, Michael R.; Johnson, Carl R.; Glick, Milton D. Journal of Organic Chemistry, 1984 , vol. 49, p. 2746 - 2748

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被引用次数: 19

摘要

The total synthesis of (-)-rothrockene, trans-1-(l-methylethenyl)-2-(2~ methyl-l-propenyl) cyclopropane, and ita enantiomer is described. Utilization of (-)-(R)-N, S-dimethyl-S- phenylsulfoximine in the synthesis allowed for resolution of a precursor, regio-and diastereoface selectivity in a Simmons-Smith cyclopropanation, determination of absolute configurations based on X-ray crystallography, and introduction of a side-chain double ...