Stereochemistry of coriamyrtin and problems of derivatives

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  • Coriamyrtin. XI. Stereochemistry of Coriamyrtin and Problems of Derivatives.

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Dihydrocoriamyrtin and α-bromocoriamyrtin were reduced with lithium aluminum hydride to afford acetals, (IV) and (V), respectively. The formation of these derivatives coupled with other evidences indicates the relative configurations of coriamyrtin to be represented by (Ia). The product of the lead tetraacetate oxidation of coriamyrtin was found to be an acetoxy-oxide (XVII) of which the correlation with the product (XVIII) of the performic acid oxidation of coriamyrtin, and also with α-bromocoriamyrtin were established. Among the two structures for dihydrocoriamyrtinpentaol, (XIb) was shown to be preferable. The problems concerning the stereo-structure of isohydrocoriamyrtin (VI), the aromatization of coriamyrtin to (XI), and some other derivatives were also investigated.

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