Absolute configuration of isoeichlerialactone

The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra-hydro-furan-2-yl]-7-(prop-1-en-2-yl)dodeca-hydro-1H-cyclo-penta-[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds o...

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Published inActa crystallographica. Section E, Structure reports online Vol. 66; no. Pt 4; pp. o879 - o880
Main Authors Fun, Hoong-Kun, Joycharat, Nantiya, Voravuthikunchai, Supayang Piyawan, Chantrapromma, Suchada
Format Journal Article
LanguageEnglish
Published United States International Union of Crystallography 20.03.2010
Subjects
Organic Papers
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Summary:The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra-hydro-furan-2-yl]-7-(prop-1-en-2-yl)dodeca-hydro-1H-cyclo-penta-[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds of Aglaia forbesii. The mol-ecule has three fused rings and all rings are in trans-fused. The two cyclo-hexane rings are in standard chair conformations and the cyclo-pentane ring adopts an envelope conformation. Its absolute configuration was determined by the refinement of the Flack parameter to 0.26 (17). In the crystal, mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds.
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Permanent address: Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.
Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.
Thomson Reuters ResearcherID: A-3561-2009.
ISSN:1600-5368
1600-5368
DOI:10.1107/S1600536810009499