Substituted Oxocanes by Intramolecular Allylboration Reactions. Entry to an Efficient Synthesis of (+)-Laurencin

Substituted Oxocanes by Intramolecular Allylboration Reactions. Entry to an Efficient Synthesis of (+)-Laurencin

Δ5-Oxocenes, such as cis-3-hydroxy-2-vinyl-Δ5-oxocenes, can be generated by an intramolecular aldehyde−allylboration reaction. This allowed a rapid and stereoselective access to the trisubstituted oxocene 24 which had been transformed by the Holmes group into (+)-laurencin. The key feature of this e...

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Veröffentlicht in:Journal of the American Chemical Society 1997-08, Vol.119 (32), p.7499-7504
Hauptverfasser: Krüger, Jochen, Hoffmann, Reinhard W
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creator Krüger, Jochen
Hoffmann, Reinhard W
description Δ5-Oxocenes, such as cis-3-hydroxy-2-vinyl-Δ5-oxocenes, can be generated by an intramolecular aldehyde−allylboration reaction. This allowed a rapid and stereoselective access to the trisubstituted oxocene 24 which had been transformed by the Holmes group into (+)-laurencin. The key feature of this effective intramolecular allylboration reaction is that both the aldehyde and the allylboronate functionality have been generated in a masked form in situ. They are liberated by an aqueous workup which initiates the ring closure reaction.
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title Substituted Oxocanes by Intramolecular Allylboration Reactions. Entry to an Efficient Synthesis of (+)-Laurencin
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