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

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Author(s): Vratislav Langer | Dalma Gyepesová | Marian Koman | Peter Kapitán | Matej Babjak | Tibor Gracza | Miroslav Koóš

Journal: Molecules
ISSN 1420-3049

Volume: 8;
Issue: 7;
Start page: 599;
Date: 2003;
Original page

Keywords: Lactones | palladium(II)-catalysis | oxycarbonylation | X-ray diffraction analysis | conformation

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.