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UBC Theses and Dissertations

Synthesis and conformational studies of 11-(1,3-Dithian-2-YL)-13-tetradecanolide Spracklin, Douglas Kenneth


11-(1,3-Dithian-2-yl)-13-tetradecanolide (71) was synthesized in a ten step sequence in approximately 3% overall yield. Alkylation of this compound with methyl iodide yielded a 6:1 mixture of diastereomers 72 and 73, the major isomer being 72. The stereochemistry at C-2 of these compounds was determined by their conversion to 74 and 75. respectively, whose stereochemistry was known. Results of molecular mechanics calculations suggest that the alkylation reaction proceeds through either of the low energy [3335] or [3344] conformations, both of which give rise to the observed product ratio.[See Thesis for Diagram]

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