Studies Directed Toward The Diastereocontrolled Synthesis Of Heritol

Abstract

3,3-Dichloro-4-indanyloxetan-2-one was synthesized and its double ring expansion in the presence of the Lewis acid magnesium bromide was investigated, which resulted only in a trans-fused butyrolactone in 25% yield. Of the natural products containing butyrolactones fused to 6-membered rings, trans is more common. This method of double ring expansion can be applied to the synthesis of the natural product heritol, whose core structure contains the butenolide moiety. A model study of the double ring expansion was performed with 3-chloro-4-indanyl-3-methyloxetane-2-one B6, but this study was not completed.

In order to apply the double ring expansion methodology to synthesize heritol, the preparation of 5-methoxy-3,6-dimethyl-1-indanone starting with p-methylacetophenone, was attempted. Since two key references discussing the synthesis of ester C6 were found much later and some of the results were not reproducible, it's completion was not achieved.

The synthesis of 3,3-disubstituted-4-indanyl-ẞ-lactones via [2+2] cycloaddition of 1-indanecarboxaldehyde with disubstituted ketenes and subsequent ring expansion, along with the attempted synthesis of 5-methoxy-3,6- dimethyl-1-indanone, the starting material for heritol synthesis, are discussed in detail.

Date of Award	2007
Original language	American English
Awarding Institution	Eastern Illinois University
Supervisor	Edward Treadwell (Supervisor)