Journal of Organic Chemistry p. 2746 - 2748 (1984)
Update date:2022-08-04
Topics:
Barbachyn, Michael R.
Johnson, Carl R.
Glick, Milton D.
The total synthesis of (-)-rothrockene, trans-1-(1-methylethenyl)-2-(2-methyl-1-propenyl)cyclopropane, and its 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 configuration based on X-ray crystallography, and introduction of a side-chain double bond.The absolute configuration of the natural substance is shown to be 1R,2S.
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