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Molecules 2003, 8(7), 599-606; doi:10.3390/80700599
Article

Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one

1,* , 2, 3, 4, 4, 4 and 5
1 Department of Environmental Inorganic Chemistry, Chalmers University of Technology, SE-41296 Göteborg, Sweden 2 Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-84536 Bratislava, Slovakia 3 Department of Inorganic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia 4 Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia 5 Institute of Chemistry, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 4 September 2002 / Revised: 25 June 2003 / Accepted: 28 June 2003 / Published: 15 July 2003
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Abstract

The absolute configuration at two newly formed stereogenic centres (5S, 7S) during the key steps of the total synthesis of naturally occuring goniothalesdiol was established by single-crystal X-ray diffraction analysis relative to stereocentres (1S, 8R) of the title compound (alternatively named 3,6-anhydro-2-deoxy-6-phenyl-L-ido-1,4-hexonolactone, C12H12O4). The conformation of both 5-membered lactone and furanose fused rings is also discussed.
Keywords: Lactones; palladium(II)-catalysis; oxycarbonylation; X-ray diffraction analysis; conformation Lactones; palladium(II)-catalysis; oxycarbonylation; X-ray diffraction analysis; conformation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Langer, V.; Gyepesová, D.; Koman, M.; Kapitán, P.; Babjak, M.; Gracza, T.; Koóš, M. Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one. Molecules 2003, 8, 599-606.

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