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Absolute stereochemistry of altersolanol a and alterporriols
Author(s) -
Kanamaru Saki,
Honma Miho,
Murakami Takanori,
Tsushima Taro,
Kudo Shinji,
Tanaka Kazuaki,
Nihei KenIchi,
Nehira Tatsuo,
Hashimoto Masaru
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21035
Subject(s) - chemistry , chirality (physics) , absolute configuration , stereochemistry , circular dichroism , dimer , cotton effect , derivative (finance) , spectral line , atropisomer , vibrational circular dichroism , crystallography , chiral symmetry , organic chemistry , physics , quantum mechanics , astronomy , financial economics , nambu–jona lasinio model , economics , quark
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 . Chirality, 2012. © 2011 Wiley Periodicals, Inc.