Total Synthesis of Natural (+)-Spatol. Confirmation of The Absolute Stereostructure

Article abstract of DOI:10.1016/S0040-4020(01)81205-9

Total synthesis of optically pure spatol (+)-1 was achieved by employing asymmetric (2+2) photocycloaddition of the optically pure 12 with cyclopentenone ethylene ketal.The two major photocycloadducts 14, 15 were separately converted into the cis,anti,cis-tricyclo<5.3.0.0^2,6>decane 9 and then to the sulfonium 11.Coupling of 11 through ylide with optically active epoxyaldehyde 24 provided optically pure 1 with definite absolute configuration.