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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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A delicate balance of energetics. Subtleties associated with alpha-ketol-based bridge migration to afford 9-keto-10beta-p-methoxybenzyloxytaxanes.

The feasibility of the title reaction has been pursued for the purpose of advancing a concise total synthesis of Taxol. Of the two closely related series examined, the first featured an exo-methylene group at C4. The second consisted of an alpha-epoxide at that site. Strikingly, the olefinic construct proved inert to attempted alpha-ketol rearrangement. In contrast, the oxiranyl derivative isomerized smoothly. The reaction sequence associated with arrival at taxane 18 is short (15 steps from a D-camphor derivative) and notably efficient. The thermodynamic issues that are raised by this investigation have been clarified by an assessment of molecular mechanics-derived (MM3) steric energy calculations.[1]

References

  1. A delicate balance of energetics. Subtleties associated with alpha-ketol-based bridge migration to afford 9-keto-10beta-p-methoxybenzyloxytaxanes. Paquette, L.A., Lo, H.Y., Hofferberth, J.E., Gallucci, J.C. J. Org. Chem. (2003) [Pubmed]
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