Abstract
The structure of the natural product lawinal [systematic name: (-)-(2S)-5,7-dihy-droxy-6-methyl-4-oxo-2-phenyl-chromane-8-carbaldehyde, C17H14O5] at 150 K is reported. The compound crystallizes with monoclinic (I2) symmetry and with Z' = 2. The absolute configuration could not be determined reliably from X-ray analysis only. However, our analysis returns the S-configuration at the C-2 position, consistent with previous stereochemical assignment from specific rotation. The independent mol-ecules form into alternating hydrogen-bonded chains with C-H⋯O=CH inter-molecular linkages that run parallel to the crystallographic a axis and are extended into the ac plane by π-π inter-actions between their phenyl substituents.
Highlights
The structure of the natural product lawinal [systematic name: (À)-(2S)-5,7dihydroxy-6-methyl-4-oxo-2-phenylchromane-8-carbaldehyde, C17H14O5] at 150 K is reported
Our analysis returns the S-configuration at the C-2 position, consistent with previous stereochemical assignment from specific rotation
The small flowering plants of the Desmos genus belong to the Annonaceae family, which comprises about 33 species and is distributed widely throughout Southern Asia and northern Australia (Brophy et al, 2002; Clement et al, 2017)
Summary
The small flowering plants of the Desmos genus belong to the Annonaceae family, which comprises about 33 species and is distributed widely throughout Southern Asia and northern Australia (Brophy et al, 2002; Clement et al, 2017). Several species of this genus have been used as Chinese folk medicines (Wu et al, 2003). We report the isolation and crystal structure of the flavonoid, (À)(2S)-5,7-dihydroxy-6-methyl-4-oxo-2-phenylchromane-8-carbaldehyde, commonly known as lawinal, isolated from the twig extract of D. dumosus
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