Tetrahedron p. 5127 - 5144 (1990)
Update date:2022-08-02
Kolb, Hartmuth C
Hoffmann, Martin R.
The rearrangement of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (1) to trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (2) has been optimized.The effect of buffer concentration (PhCO2H/KOAc) on reaction rate and yield suggests specific acid catalysis.Substitution patterns and influence of the 6-alkoxy substituent have been investigated.Applications in natural product synthesis are described.
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