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The Nature of Persistent Conformational Chirality, Racemization Mechanisms, and Predictions in Diarylether Heptanoid Cyclophane Natural Products

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Pattawong, Ommidala, Salih, M. Quamar, Rosson, Nicholas T., Beaudry, Christopher M., and Cheong, Paul Ha-Yeon

Abstract:

Restricted rotations of chemical bonds can lead to the presence of persistent conformational chirality in molecules 10 lacking stereocenters. We report the development of first-ofa- kind predictive rules that enable identification of conformational chirality and prediction of racemization barriers in the diarylether heptanoid (DAEH) natural products that do not possess...

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path is shown in Figure 7, A. The rotation of C12-C13 is found to be a common RDS for all minimum
Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

Creator:

McClintock, Sean P., Forster, Nathan, Herges, Rainer, and Haley, Michael M.

Abstract:

The synthesis of isoindazoles bearing α-ketoester and α-hydroxyester groups via the coarctate cyclization of ester terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene...

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excess CuCl,5 ester 6 needed only 4 h at 50 °C to cyclize completely to 9. The reaction could also be

ScholarsArchive@OSU

The Nature of Persistent Conformational Chirality, Racemization Mechanisms, and Predictions in Diarylether Heptanoid Cyclophane Natural Products

Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

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