title: Homodecoupled 1,1- and 1,n-ADEQUATE: Pivotal NMR Experiments for the Structure Revision of Cryptospirolepine.
abstract: Cryptospirolepine is the most structurally complex alkaloid discovered and characterized thus far from any Cryptolepis specie. Characterization of several degradants of the original, sealed NMR sample a decade after the initial report called the validity of the originally proposed structure in question. We now report the development of improved, homodecoupled variants of the 1,1- and 1,n-ADEQUATE (HD-ADEQUATE) NMR experiments; utilization of these techniques was critical to successfully resolving long-standing structural questions associated with crytospirolepine.
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA).
authors.forename: Josep
authors.initials: J
authors.lastname: Saurí
authors.affiliation: Bruker Biospin GmbH, Silberstreifen, 76287 Rheinstetten (Germany).
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Bermel
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA).
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Buevich
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA).
authors.forename: Edward C
authors.initials: EC
authors.lastname: Sherer
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA).
authors.forename: Leo A
authors.initials: LA
authors.lastname: Joyce
authors.affiliation: American Herbal Products Association, Silver Spring, MD 20910 (USA).
authors.forename: Maged H M
authors.initials: MH
authors.lastname: Sharaf
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA 15261 (USA).
authors.forename: Paul L
authors.initials: PL
authors.lastname: Schiff
authors.affiliation: Servei de Ressonància Magnètica Nuclear and Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona (Spain).
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA).
authors.forename: R Thomas
authors.initials: RT
authors.lastname: Williamson
authors.affiliation: Process & Analytical Chemistry, Merck Research Laboratories, Mailstop: 800-D133, 126 E. Scott Ave, Rahway, NJ 07065 (USA). gary.martin2@merck.com.
authors.forename: Gary E
authors.initials: GE
authors.lastname: Martin
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D031106:Cryptolepis / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D010936:Plant Extracts; D011804:Quinolines; C000607749:cryptospirolepine
keywords: DFT calculations; HD-ADEQUATE; NMR spectroscopy; cryptolepis alkaloids; homodecoupling