title: Tremorgenic indole alkaloids. Studies directed toward the assembly of the A, F, and I rings of penitrem D: observation of an unexpected stereochemical outcome.
abstract: [formula: see text] In this Letter we demonstrate the viability of a highly stereoselective tandem Mannich cyclization-grammine fragmentation/addition cascade, critical for assembly of the A and F rings of penitrem D. We also explored simultaneous execution of this tactic with concurrent construction of ring I. Reinvestigation of a model system provided an explanation for the unanticipated stereochemical outcome at C(28).
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
authors.forename: A B
authors.initials: AB
authors.lastname: Smith
authors.forename: N
authors.initials: N
authors.lastname: Kanoh
authors.forename: N
authors.initials: N
authors.lastname: Minakawa
authors.forename: J D
authors.initials: JD
authors.lastname: Rainier
authors.forename: F R
authors.initials: FR
authors.lastname: Blase
authors.forename: R A
authors.initials: RA
authors.lastname: Hartz
mesh_terms: D000470:Alkaloids / Q000009:adverse effects / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry*; D013237:Stereoisomerism; D014202:Tremor / Q000139:chemically induced*
chemical_list: D000470:Alkaloids; D007211:Indoles; D009183:Mycotoxins; C003626:tremortin