A new approach to the pancratistatin C-ring from d-glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

✍ Scribed by Gregory K. Friestad; Bruce P. Branchaud

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 257 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01325-7

✦ Synopsis

A Ferrier rearrangement and [~-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by ~hydroxyketone transposition, which allows convenient access from methyl (z-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C 1 hydroxyl to deliver the tethered aryl synthon.