Absolute structures and conformations of the spongian diterpenes spongia-13(16), 14-dien-3-one, epispongiadiol and spongiadiol

Yong, Ken W., L., Garson, Mary J. and Bernhardt, Paul V. (2009) Absolute structures and conformations of the spongian diterpenes spongia-13(16), 14-dien-3-one, epispongiadiol and spongiadiol. Acta Crystallographica Section C - Crystal Structure Communications, 65 4: o167-o170. doi:10.1107/S0108270109008816


Author Yong, Ken W., L.
Garson, Mary J.
Bernhardt, Paul V.
Title Absolute structures and conformations of the spongian diterpenes spongia-13(16), 14-dien-3-one, epispongiadiol and spongiadiol
Journal name Acta Crystallographica Section C - Crystal Structure Communications   Check publisher's open access policy
ISSN 0108-2701
1600-5759
Publication date 2009-03-25
Sub-type Article (original research)
DOI 10.1107/S0108270109008816
Volume 65
Issue 4
Start page o167
End page o170
Total pages 4
Editor G Kostorz
Place of publication Malden, MA, United States
Publisher Wiley-Blackwell Publishing
Collection year 2010
Language eng
Subject C1
030606 Structural Chemistry and Spectroscopy
970103 Expanding Knowledge in the Chemical Sciences
Formatted abstract The absolute conīŦgurations of spongia-13(16),14-dien-3-one [systematic name: 3bR,5aR,9aR,9bR)-3b,6,6,9a-tetramethyl-4,5,5a,6,8,9,9a,9b,10,11-decahydrophenanthro[1,2-c]furan-7(3bH)-one], C20H28O2, (I), epispongiadiol [systematic name: (3bR,5aR,6S,7R,9aR,9bR)-7-hydroxy-6-hydroxymethyl-3b,6,-9a-trimethyl-3b,5,5a,6,7,9,9a,9b,10,11-decahydrophenanthro-[1,2-c]furan-8(4H)-one], C20H28O4, (II), and spongiadiol [systematic name: (3bR,5aR,6S,7S,9aR,9bR)-7-hydroxy-6-hydroxymethyl-3b,6,9a-trimethyl-3b,5,5a,6,7,9,9a,9b,10,11-decahydrophenanthro[1,2-c]furan-8(4H)-one], C20H28O4, (III), were assigned by analysis of anomalous dispersion data collected at 130 K with Cu Kα radiation. Compounds (II) and (III) are epimers. The equatorial 3-hydroxyl group on the cyclohexanone ring (A) of (II) is syn with respect to the 4-hydroxymethyl group, leading to a chair conformation. In contrast, isomer (III), where the 3-hydroxyl group is anti to the 4-hydroxymethyl group, is conformationally disordered between a major chair conformer where the OH group is axial and a minor boat conformer where it is equatorial. In compound (I), a carbonyl group is present at position 3 and ring A adopts a distorted-boat conformation. 
Keyword Glossodoris-Atromarginata
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2010 Higher Education Research Data Collection
ERA 2012 Admin Only
School of Chemistry and Molecular Biosciences
 
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Created: Thu, 03 Sep 2009, 08:26:00 EST by Mr Andrew Martlew on behalf of School of Chemistry & Molecular Biosciences