6533b839fe1ef96bd12a65a9
RESEARCH PRODUCT
Total Synthesis of (-)-Hymenosetin.
Stefan WeckUlrich KauhlLars AndernachTill OpatzEckhard ThinesEckhard ThinesStefan JacobLouis P. Sandjosubject
Circular dichroismBiological ProductsCycloaddition ReactionMolecular Structure010405 organic chemistryChemistryStereochemistryOrganic ChemistryAbsolute configurationDiastereomerTotal synthesisStereoisomerism010402 general chemistry01 natural sciencesPyrrolidinones0104 chemical scienceschemistry.chemical_compoundDecalinIntramolecular forceMoietyMoleculedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-12-16 | The Journal of organic chemistry |