Dolabellane diterpenoids from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata: spectroscopic and X-ray studies of structure, stereochemistry, and conformation. X-Ray molecular structure of 3S,4S;7S,8S-diepoxy-10R,18-dihydroxydollabellane, 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane, and 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene

Huneck, S., Baxter, G. A., Cameron, A. F., Connolly, J. D., Harrison, L. J., Phillips, W. R., Rycroft, D. S. and Sim, G. A. (1986) Dolabellane diterpenoids from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata: spectroscopic and X-ray studies of structure, stereochemistry, and conformation. X-Ray molecular structure of 3S,4S;7S,8S-diepoxy-10R,18-dihydroxydollabellane, 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane, and 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene. Journal of the Chemical Society: Perkin Transactions 1, pp. 809-814. (doi:10.1039/P19860000809)

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Abstract

The dolabellane diterpenoids 10R,18-diacetoxy-3S,4S;7S,8S-diepoxydolabellane (barbilycopodin) (1), 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene (12), 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane (4), and 18-hydroxydolabell-7E-en-3-one (14) have been isolated from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata. The 1H and 13C n.m.r. spectroscopic properties of the compounds and some of their transformation products are described. The structures, relative stereochemistries, and conformations of compounds (4), (12), and 3S,4S;7S,8S-diepoxy-10R,18-dihydroxydollabellane (2) were defined by X-ray crystallographic studies. The eleven-membered ring has essentially the same conformation in compounds (2), (4), and (12), a conformation which has been characterised as a low-energy form of cycloundeca-1,5-diene by molecular-mechanics calculations.

Item Type:Articles
Keywords:Liverwort, natural product chemistry, NMR spectroscopy.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Connolly, Professor Joseph and Rycroft, Dr David
Authors: Huneck, S., Baxter, G. A., Cameron, A. F., Connolly, J. D., Harrison, L. J., Phillips, W. R., Rycroft, D. S., and Sim, G. A.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of the Chemical Society: Perkin Transactions 1
Journal Abbr.:J. Chem. Soc., Perkin Trans. 1
Publisher:Royal Society of Chemistry
ISSN:0300-922X
ISSN (Online):2050-8255

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