Total synthesis and stereochemistry of pinnatoxins B and C.
[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.
Matsuura
Fumiyoshi
F
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Hao
Junliang
J
Reents
Reinhard
R
Kishi
Yoshito
Y
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
D000438:Alcohols; D000470:Alkaloids; D013141:Spiro Compounds; C519414:pinnatoxin B; C519415:pinnatoxin C