Synthesis and Absolute Configuration of (-)-Rothrockene, a Non-Head-To-Tail Monoterpene

Article abstract of DOI:10.1021/jo00189a020

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.