title: Total synthesis and stereochemistry of pinnatoxins B and C.
abstract: [Structure: see text] Pinnatoxins B and C were synthesized from diols (34R)-3b and (34S)-3a, respectively, in a stereochemically controlled manner. Through extensive analysis of the 1H NMR spectra of synthetic PnTXs B and C, the diagnostic NMR signals were first identified to differentiate (34S)- and (34R)-diastereomers and then used to establish the C34 configuration of natural PnTXs B and C as 34S and 34R, respectively.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
authors.forename: Fumiyoshi
authors.initials: F
authors.lastname: Matsuura
authors.forename: Junliang
authors.initials: J
authors.lastname: Hao
authors.forename: Reinhard
authors.initials: R
authors.lastname: Reents
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Kishi
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000470:Alkaloids; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012758:Shellfish; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000470:Alkaloids; D013141:Spiro Compounds; C519414:pinnatoxin B; C519415:pinnatoxin C