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Stereoselective synthesis of acortatarins a and B |
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| Authors: | Jacqueline M Wurst Alyssa L Verano Derek S Tan |
| Institution: | Tri-Institutional Training Program in Chemical Biology, Pharmacology Program-Weill Cornell Graduate School of Medical Sciences, Molecular Pharmacology & Chemistry Program, and Tri-Institutional Research Program, Memorial Sloan-Kettering Cancer Center , 1275 York Avenue, Box 422, New York, New York 10065, United States. |
| 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. |
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