Jörg Mühlbacher

MD‐based CD calculations for the assignment of the absolute axial configuration of the naphthylisoquinoline alkaloid dioncophylline A

The circular dichroism (CD) of the biaryl alkaloid dioncophylline A (2) was investigated by CD calculations; the structures were generated by molecular dynamics (MD) simulations using the force field CVFF. From these structures the CD spectra were calculated with the semiempirical method CNDO/2S. Summing up the single CD spectra yielded the final spectrum. In contrast to our earlier method based on the Boltzmann weighting, the MD‐assisted approach permitted to assign the flexible biaryl axis of dioncophylline A (2), which is found to be P.

Revised Structure of Antidesmone, an Unusual Alkaloid from Tropical Antidesma Plants (Euphorbiaceae)

Abstract The structure of antidesmone, an alkaloid from Antidesma membranaceum Mull. Arg. and A. venosum E. Mey. (Euphorbiaceae), was revised to be (S)-4,8-dioxo-3-methoxy-2-methyl-5-n-octyl-1,4,5,6,7,8-hexahydroquinoline [(S)-2], not the isoquinoline derivative 1, as assumed previously. The revision was initiated by biosynthetic feeding experiments of one of our groups.

The absolute configuration of the mushroom metabolites involutin and chamonixin

Abstract The absolute configurations of the cyclopentanoid fungal metabolites involutin (1) and chamonixin (2) have been determined by application of the high-field 1H NMR variant of Moshers method. The experimental results are supported by quantum chemical calculations.

En route to the first stereoselective synthesis of axially chiral biscarbazole alkaloids

The first stereoselective synthesis of an axially chiral biscarbazole has been achieved, by application of the ‘lactone concept’.