Synthesis, crystal structure and molecular conformation of (±)-1-oxoferruginol and (±)-shonanol
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Swastik Mondal
Abstract
(±)-1-oxoferruginol and (±)-shonanol, two potential intermediates in the synthesis of tricyclic diterpenoid ferruginol, have been prepared and crystal structures of the compounds have been investigated using single-crystal X-ray diffraction data. The methyl groups of the isopropyl moiety in (±)-shonanol are disordered over two positions with occupation factors 0.65(1) and 0.35(1), respectively. Although the chemical structures of two compounds are very similar, a C—C single bond in the terminal six-membered ring of (±)-1-oxoferruginol is replaced by a C=C bond in (±)-shonanol, the quantitative isostructurality index calculations indicate that the structures are not isostructural. Intermolecular O—H…O hydrogen bonds between pairs of molecules in the compounds related by center of inversion lead to characteristic dimers forming R22(16) rings. The molecular conformation of (±)-1-oxoferruginol obtained from the semi-empirical quantum mechanical AM1 calculation shows good agreement with the X-ray structures.
© 2004 Oldenbourg Wissenschaftsverlag GmbH
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Articles in the same Issue
- Structural changes upon the temperature dependent C2/c → P21/c phase transition in LiMe3+Si2O6 clinopyroxenes, Me = Cr, Ga, Fe, V, Sc and In
- X-ray diffraction study of decagonal Al—Co—Ni as a function of composition
- The correlation between metal oxidation state and bond valence parameters for M—O bonds (M = V, Fe and Cu). A simple method to search for the metal oxidation-state independent parameter pairs
- The crystal structures of Hg7Se3O13H2 and Hg8Se4O17H2 — two mixed-valent mercury oxoselenium compounds with a multifarious crystal chemistry
- Calculated growth form of melilites
- Similarities between the clathrasils DOH, DDR, MEP and MTN
- Thermal expansion, elastic and thermoelastic properties including crystal structure analyses of K-, Rb- and Cs-nitrilotriacetates
- Dichloro(cyclohexilidene-1-methylene)(phenyl)Te(IV). Looking for the theoretical treatment
- Synthesis, crystal structure and molecular conformation of (±)-1-oxoferruginol and (±)-shonanol
- Triphenylphosphine adducts of silver di-iso-propyl dithiophosphate
- In-situ pressure crystallization and X-ray diffraction study of 1,1,2,2-tetrachloroethane at 0.5 GPa
- Books Received
