Synthese und Geruch von (Z)-Dehydro-homo-β-santalol

Summary Guided by molecular modeling studies, the synthesis of the title compound is described. The organoleptic evaluation proved the predicted real sandal like odour of (Z)-dehydro-homo--santalol.

Aus den Diplomarbeiten von C.P. (1991), I.P. und B.Ö. (1992), Universität Wien     

Conformational calculations on odoriferous molecules of sandalwood,I. The search for the odoriferous principle of sandalwood oil

The conformations of two relatively rigid molecules with sandalwood odor have been investigated by molecular mechanics and the semiempirical method AM1. A comparison between both geometries shows that a common structural element exists in the relative rearrangement of a carbinol function and a quarternary carbon atom. The distance of these two centers as well as the electron density agree well in both structures.

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Rechnungen zur Konformation von Molekülen mit Sandelholzgeruch, 1. Mitt.: Die Suche nach dem Geruchsprinzip des Sandelholzöles

Zusammenfassung Die Konformationen zweier relativ starrer Moleküle mit Sandelholzgeruch wurden mit molekularmechanischer und mit einer semiempirischen Methode (AM1) bestimmt. Ein Vergleich der beiden molekularer Geometrien zeigt ein gemeinsames Strukturelement und zwar die relative Anordnung der Carbinolfunktion zu einem quartären Kohlenstoffatom. Sowohl deren Abstand als auch deren Elektronendichte stimmen in beiden Verbindungen überein.

     

Surface comparisons of some odour molecules: Conformational calculations on sandalwood odour V

Summary Molecular surface comparison seems to be a very suitable tool for the investigation of small differences between biologically active and inactive compounds of the same structural type. A fast method for such comparisons, based on volume matching followed by the estimation of comparable surface dots, is presented and applied on a few selected sandalwood odour molecules.     

(Z)-homo-β-Santalol: Synthese und Geruch

Summary The synthesis of the title compound is described. Starting with the -alkylation ofhomo-norcamphor followed by aWittig reaction, aTebbe transformation, and aDIBAH ester-reduction as the most important reactions of a 5 step sequence, (Z)-homo--santalol was obtained, which exhibits the typical precious sandalwood odour. The moderate increase of the volume of the bulky group obviously does not alter the odour quality sandalwood of this new -santalol analogue.

     

Synthese und Geruch von (E)- und (Z)-bis-homo-ß-Santalol

Summary The synthesis of the title compounds is described. Guided by theoretical considerations and molecular modeling studies, the influence of the bulky group opposite to the osmophorically important primary hydroxyl function on the odour impression is determined. The organoleptic evaluation proved the predicted sandal like odour of the (Z)-isomer and its also predicted absence with (E)-isomer. A moderate increase of the volume of the bulky group shows no influence on the sandalwood odour of the new analogue.

     

Synthesis of Polysantol and related sandalwood-type odorants using magnesium α-bromoketone enolates

The syntheses of the commercial sandalwood-type odorant Polysantol^® and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, α-campholenic aldehyde and different α-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30-56% overall yields.     

Die geruchsintensivsten Inhaltsstoffe des ostindischen Sandelholzöles

The most odour intensive constituents of east indian sandal wood oil are -santalol, -santalal and -santalene. This has been proved by a thorough GLC-investigation in combination with the sniffing technique of seven fractions of this highly priced essential oil, which have been obtained by TLC on silica-cellulose plates with simultaneous organoleptic evaluation. Using the headspace analysis these results could be confirmed and further the distribution of the main odour components was obtained in headspace at 37° and 80°.

Herrn Prof. DDr. h. c.K. Kratzl in dankbarer Verehrung mit den besten Wünschen zum 70. Geburtstag gewidmet.     

A rapid method for molecular shape comparison of medium-sized molecules. Conformational calculations on sandalwood odor,IV

Summary A fast method of a surface comparison of two or more molecules to be matched is presented. The Van der Waals surfaces of molecules are described by points calculated as the intersection of grid lines with the molecular surface. The mean surface of various molecules with the same biological activity can be constructed. It is used for further comparisons with similar molecules lacking this activity. Deviations of any molecular surface from the mean surface can be mapped onto the surface. The method was tested on a distinct group of sandalwood odor molecules and it was shown that such matching and comparison procedures are useful in the investigation of odor structure-activity relationships proposed as CAFD (computer aided fragrance design).Dedicated to Prof. Dr. W. Fleischhacker, on occasion of his 60th anniversary     

Synthesen in der Isocamphanreihe, 37. Mitt.: Analytik und Geruch isomerer cyclischer Acetale mit Norbornanstruktur

Summary The separation of a complex mixture of a fragrance material into its isomers is described. Instead of an odour of sandalwood the mixture exhibits mainly a mushroom odour but also the pure isomers show other organoleptic qualities. The structure of two isomers could be ascertained mainly by¹³C- and¹H-NMR-measurements, for two isomers a structure proposal is given.

Herrn Prof. Dr. Wilhelm Fleischhacker mit den besten Wünschen zum 60. Geburtstag gewidmet