Systematic assignment of the configuration of flexible natural products by spectroscopic and computational methods: the bistramide C analysis.
[reaction: see text] The combination of NMR NOE, chemical shift, and J-coupling measurements with molar rotation and circular dichroism (CD) determinations, including RI-DFT BP86/aug-cc-pVDZ calculations, reduced a candidate pool of 1024 possible stereoisomers of (+)-bistramide C to a single absolute configuration assignment for the 10 stereogenic carbons of the marine natural product.
Zuber
Gérard
G
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Goldsmith
Michael-Rock
MR
Hopkins
Tamara D
TD
Beratan
David N
DN
Wipf
Peter
P
D001688:Biological Products / Q000032:analysis* / Q000737:chemistry*; D002942:Circular Dichroism; D004988:Ethers, Cyclic / Q000032:analysis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D001688:Biological Products; D004988:Ethers, Cyclic; C456580:bistramide C