Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-oneAuthor(s): Vratislav Langer | Dalma GyepesovÃƒÂ¡ | Marian Koman | Peter KapitÃƒÂ¡n | Matej Babjak | Tibor Gracza | Miroslav KoÃƒÂ³Ã…Â¡
Journal: Molecules ISSN 1420-3049
Volume: 8; Issue: 7; Start page: 599; Date: 2003;
Keywords: Lactones | palladium(II)-catalysis | oxycarbonylation | X-ray diffraction analysis | conformation
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.