| Abstract
| - Highly stereoselective asymmetric boronic ester chemistry has beenused to install all three chiral centersin a convergent synthesis of highly pure stegobinone, the epimericallylabile pheromone of the drugstore beetle,Stegobium paniceum, and the furniture beetle, Anobiumpunctatum. Asymmetric centers were installed via thereactionof (dichloromethyl)lithium with 1,2-dicyclohexylethane-1,2-diolboronic esters. The synthetic strategy utilizes acommon (α-chloroalkyl)boronic ester intermediate as the sourceof both segments and all of the asymmetry of thetarget molecule. The two segments are joined by an aldolcondensation and converted to stegobiol, a minor componentof the S. paniceum pheromone and presumably the biogeneticprecursor of stegobinone. Stegobiol is stable andeasily purified, and is easily converted to pure stegobinone in asingle oxidation step.
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