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

✍ Scribed by J. KRUEGER; R. W. HOFFMANN

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Substituted Oxocanes by Intramolecular Allylboration Reactions. Entry to an Efficient Synthesis of (+)-Laurencin. -Ξ΄5-Oxocenes such as (II) can be generated by an intramolecular aldehyde-allylboration reaction.

The key feature of this reaction is that both the aldehyde and the allylboronate functionality are generated in a masked form in situ. They are liberated by an aqueous work-up which initiates the ring closure reaction. An application of this methodology starts with the chiral (III) for the preparation of ( IV) and its transformation into the trisubstituted oxocene (V). The conversion of (VI) into the title compound (VII) is known. -(KRUEGER, J.

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