Abstract
The carbon resonances were assigned for the bark beetle pheromones frontalin, exo-brevicomin, endo-brevicomin, α-multistriatin, and for the γ and δ isomers of multistriatin. The chemical shift changes that occurred with changes in orientation of the various alkyl substituents of the 6,8-dioxabicyclo (3.2.1)octane system were noted for carbons α, β, γ, and δ to the substituent in question. The γ effects observed for the ring carbons of the multistriatin isomers confirmed the relative stereochemistry of these compounds. Several small but significant δ effects were also observed. Only γ effects involving a changing relationship with one carbon can be considered reliable for stereochemical inferences in such sterically crowded ring systems.
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