Total synthesis of natural (+)-spatol (cas 76520-52-0). Confirmation of the absolute stereostructure

Add time:07/12/2019    Source:sciencedirect.com

Total synthesis of optically pure spatol (+)-1 was achieved by employing asymmetric (2+2) photocycloaddition of the optically pure butenolide 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.

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