1. Stereoselective synthesis of acortatarins A and B.
- Author
-
Wurst JM, Verano AL, and Tan DS
- Subjects
- Alkaloids chemistry, Catalysis, Mercury chemistry, Molecular Structure, Morpholines chemistry, Plant Roots chemistry, Pyrroles chemistry, Spiro Compounds chemistry, Acorus chemistry, Alkaloids chemical synthesis, Morpholines chemical synthesis, Pyrroles chemical synthesis, Spiro Compounds chemical synthesis
- Abstract
Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.
- Published
- 2012
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