- Total synthesis of the naturally occurring furanoid fatty acid, F5
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The furanoid fatty acid F5 has been synthesized using a mercury(II) catalyzed isomerization of 2-(1,2-oxiranylcyclododecyl)-3-nonyn-2-ol.
- Marson, Charles M.,Harper, Steven
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p. 333 - 334
(2007/10/03)
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- Highly stereoselective synthesis of bicyclo[n.3.0]alkanes by titanium tetrachloride promoted [3 + 2] cycloaddition of allylsilanes and 1-acetylcycloalkenes
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The titanium tetrachloride promoted reaction of allylsilanes 1 with 1-acetylcyclohexene is shown to afford the silylbicyclo[4.3.0]nonanes 9 ([3 + 2] cycloaddition products) along with the 1-acetyl-2-allylcyclohexane 4 (Hosomi-Sakurai product). Here we report that systematic variation of the substituents at the silicon atom of 1 allows suppression of the classical Hosomi Sakurai reaction in favor of the [3+2] cycloaddition. Cycloaddition of the allylsilanes 1d, 1i, and 1k with 1-acetylcycloalkenes 10, containing a 5-, 6-, 7-, 8-, or 12-membered ring, gives rise to the corresponding silylbicyclo[n.3.0]alkanes 11-13. The cycloaddition of allyltriisopropylsilane (1k) and 1-acetyl-2-methylcycloalkenes 15 provides silylbicyclo[n.3.0]alkanes 16 with two contiguous quaternary carbon centers. The stereochemistry of the silylbicyclo[n.3.0]alkanes 11a-c and 14 is unambiguously determined by X-ray analysis and 13C NMR spectroscopy.
- Knoelker, Hans-Joachim,Foitzik, Norbert,Goesmann, Helmut,Graf, Regina,Jones, Peter G.,Wanzl, Guenter
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p. 538 - 551
(2007/10/03)
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- Musk-like scents and their manufacture
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New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.
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