| RRC ID |
47576
|
| Author |
Kanamaru S, Honma M, Murakami T, Tsushima T, Kudo S, Tanaka K, Nihei K, Nehira T, Hashimoto M.
|
| Title |
Absolute stereochemistry of altersolanol A and alterporriols.
|
| Journal |
Chirality
|
| Abstract |
The absolute stereochemistry of altersolanol A (1) was established by observing a positive exciton couplet in the circular dichroism (CD) spectrum of the C3,C4-O-bis(2-naphthoyl) derivative 10 and by chemical correlations with known compound 8. Before the discussion, the relative stereochemistry of 1 was confirmed by X-ray crystallographic analysis. The shielding effect at C7'-OMe group by C1-O-benzoylation established the relative stereochemical relationship between the C8-C8' axial bonding and the C1-C4/C1'-C4' polyol moieties of alterporriols E (3), an atropisomer of the C8-C8' dimer of 1. As 3 could be obtained by dimerization of 1 in vitro, the absolute configuration of its central chirality elements (C1-C4) must be identical to those of 1. Spectral comparison between the experimental and theoretical CD spectra supported the above conclusion. Axial stereochemistry of novel C4-O-deoxy dimeric derivatives, alterporriols F (4) and G (5), were also revealed by comparison of their CD spectra to those of 2 and 3.
|
| Volume |
24(2)
|
| Pages |
137-46
|
| Published |
2012-2-1
|
| DOI |
10.1002/chir.21035
|
| PMID |
22180221
|
| MeSH |
Anthraquinones / chemistry*
Circular Dichroism
Dimerization
Magnetic Resonance Spectroscopy
Molecular Structure
Pigments, Biological / chemistry
Saccharomycetales / chemistry
Stereoisomerism
|
| IF |
2.171
|
| Times Cited |
15
|
|
WOS Category
|
PHARMACOLOGY & PHARMACY
CHEMISTRY, ANALYTICAL
CHEMISTRY, MEDICINAL
CHEMISTRY, ORGANIC
|
| Resource |
| General Microbes |
JCM 13156 |
