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δ-Santalolanaloga I Synthesen in der Isocamphanreihe, 27. Mitt.
Authors:Gerhard Buchbauer  Gabriele Püspök  Adelheid Angermayer  Elisabeth Silbernagel  Marisa Manz
Institution:(1) Institut für Pharmazeutische Chemie, Universität Wien, A-1090 Wien, Österreich
Abstract:The synthesis of 4-(3,3-dimethyl-2-exo-norbornyl)-2-methyl-2-buten-1-ol (5), an analogue of delta-santalol (1) has been described. One route to5 starts with isocamphenilanyl propionic acid (8) which can be prepared in 4 steps from isocamphenilanic acid (9). Also 4 steps lead from8 to the target molecule5 with an overall yield of 24%. By a second and more convergent route, starting from the very easily obtainable bicyclic ketone19, the allylic alcohol5 could be obtained again in 4 steps, but this time with an overall yield of 1.3%. A new and easy synthesis of isocamphenilanyl acetic acid (15), a potential starting material to5, has been described, also the preparation of some new isocamphane derivatives.
26. Mitt:Buchbauer G,Pernold W,Ittner M,Ahmadi MF,Dobner R,Reidinger R (1985) Monatsh Chem 116: 1209
Keywords:Aldol Reaction  Allylic alcohol  Allylic oxidation  1  2-bis-(3  3-Dimethyl-2-exo-norbornyl)-ethane  4-(3  3-Dimethyl-2-exo-norbornyl)-2-methylbut-2-en-1-ol  Isocamphane derivatives  Isocamphenilanyl acetic acid  Odour  Selenium dioxide
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