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
General Microbes JCM 13156