I. Synthesis of dl-cis-Tetrahydroeremophilone. II. Studies on Systems Free from Angular Strain

Citation

Murayama, Stanley Tetsu (1969) I. Synthesis of dl-cis-Tetrahydroeremophilone. II. Studies on Systems Free from Angular Strain. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/EF19-GE34. https://resolver.caltech.edu/CaltechTHESIS:03232017-140452739

Abstract

I. The total synthesis of racemic cis-tetrahydroeremophilone (17) has been achieved. The key feature of the synthesis was a solvolytic cyclization that proceeded through a symmetrical cation 41 and gave rise to two major products, one of which had the stereochemistry required for the synthesis of tetrahydroeremophilone.

II. Attempts on the synthesis of the alcohol 1 have been investigated in three related reaction sequences (Schemes 1, 4, 5, and 6). Although none of the reaction sequences gave the desired alcohol 1 that was intended for use in a solvolysis study, an unexpected product, the keto acetate 48, resulted in one sequence and afforded adamantanone (44) upon chromatography on alumina.

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