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Published in

American Chemical Society, Journal of Organic Chemistry, 1(81), p. 215-228, 2015

DOI: 10.1021/acs.joc.5b02526

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Total Synthesis of (-)-Hymenosetin

This paper is available in a repository.
This paper is available in a repository.

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Abstract

The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.