title: Stereoselective synthesis of acortatarins A and B.
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.
authors.affiliation: Tri-Institutional Training Program in Chemical Biology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10065, USA.
authors.forename: Jacqueline M
authors.initials: JM
authors.lastname: Wurst
authors.forename: Alyssa L
authors.initials: AL
authors.lastname: Verano
authors.forename: Derek S
authors.initials: DS
authors.lastname: Tan
mesh_terms: D029023:Acorus / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008628:Mercury / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D009025:Morpholines; D011758:Pyrroles; D013141:Spiro Compounds; C550646:acortatarin A; C550647:acortatarin B; D008628:Mercury