Journal article
A new approach to the pancratistatin C-ring from d-glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations
Tetrahedron letters, Vol.38(34), pp.5933-5936
1997
DOI: 10.1016/S0040-4039(97)01325-7
Abstract
A Ferrier rearrangement and β-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 β-hydroxyketone transposition, which allows convenient access from methyl α- d-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon. Graphic
Details
- Title: Subtitle
- A new approach to the pancratistatin C-ring from d-glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations
- Creators
- Gregory K FriestadBruce P Branchaud
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.38(34), pp.5933-5936
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/S0040-4039(97)01325-7
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Language
- English
- Date published
- 1997
- Academic Unit
- Chemistry
- Record Identifier
- 9983985865802771
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