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Synthesis and Olfactoric Activity of Keto-β-santalol and Methoxy-β-santalol by Gerhard Buchbauer; Helmut Spreitzer; Friederike Zechmeister-Machhart; Alexander Klinsky; Petra Weiβ-Greiler; Peter Wolschann is a Chemistry article available to read on EtoBox.

What is Synthesis and Olfactoric Activity of Keto-β-santalol and Methoxy-β-santalol about?

In extension of structure-activity relationship inve stigations on ~-santalol , where the shape of the molecular surface was found to be of high importance, the influence of the electrostatic properties of the molecules was investigated. Two derivatives of ~-santalol with similar molecular shape but with an oxygen atom instead of carbon atoms were synthesized: keto-ji-sant alol and methoxy-ji-santalol. These two oxygen-containing santalol analogues were synthesized by total sy ntheses starting from apocamphenilone. A common intermediate for both target molecules, an appropriate bic yclic ketoaldehyde, proved to be inapplicable. Therefore methoxy-Bvsant alol was prep ared by insertion of an eth yldioxolane sidechain into apoc amphenilone and completing the synthesis by five additional steps. Kcro-jf-santalol was prepared on a con vergent route by insertion of the already prefabricated sidechain into the starting ketone, followed by one additional step. The presence of the second oxygen atom leads to the complete loss of the odour, which is the eviden ce that apart from the molecular shape, the electrostatic potential has to be taken into account in molecular similarity studies of th

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Author

Gerhard Buchbauer; Helmut Spreitzer; Friederike Zechmeister-Machhart; Alexander Klinsky; Petra Weiβ-Greiler; Peter Wolschann

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0223-5234)

Published

1998

Language

EN

Field

Chemistry (Physical Sciences)