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UBC Theses and Dissertations

Synthesis and conformational studies of 10, 10-dimethyltridecanolide Hu, Thomas Qiuxiong


The synthesis of 10,10-dimethyltridecanolide (42) was achieved via a fifteen-step sequence in 9% overall yield. The hydrolysis of macrolides 42, 35, and ester 109 was used to probe the conformational behavior of macrolide 42. The results of this study were rationalized through molecular mechanics (MM2) calculations of conformations for macrolide 42. MM2 studies confirmed initial conformational analyses that macrolide 42 should exist predominantly in the [3434] conformation 42a. More importantly, they also revealed the existence of a [3344] conformation 42f. Hydrolysis studies showed that macrolides 42 and 35 hydrolyzed more slowly than ester 109 due to the steric effect of the intermediates. They also suggested that the minor conformation 42f very likely controlled the hydrolysis process of macrolide 42. [Formula Omitted]

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