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.
Original language | English (US) |
---|---|
Pages (from-to) | 5933-5936 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 38 |
Issue number | 34 |
DOIs | |
State | Published - Aug 1997 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry