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

Vratislav Langer 1,* email, Dalma Gyepesová 2 , Marian Koman 3 , Peter Kapitán 4 , Matej Babjak 4 , Tibor Gracza 4  and Miroslav Koóš 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; in revised form: 25 June 2003 / Accepted: 28 June 2003 / Published: 15 July 2003
PDF Full-text Download PDF Full-Text [170 KB, uploaded 30 September 2008 19:38 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

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.

AMA Style

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(7):599-606.

Chicago/Turabian Style

Langer, Vratislav; Gyepesová, Dalma; Koman, Marian; Kapitán, Peter; Babjak, Matej; Gracza, Tibor; Koóš, Miroslav. 2003. "Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one." Molecules 8, no. 7: 599-606.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert