The use of d-mannitol-derived C2-symmetric trienes in tandem metathesis reactions towards valuable lactones |
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Authors: | Nassima Riache |
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Affiliation: | Laboratoire de Chimie et Biochimie des Substances Naturelles, Muséum National d'Histoire Naturelle, CNRS, 57 rue Cuvier (CP 54), 75005 Paris, France |
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Abstract: | Chiral lactones were synthesized from d-mannitol. C2-symmetric triene precursors were constructed with a central relay-olefin allowing the key domino ring-closing metathesis to be achieved. It led to the symmetrical cleavage of the substrate and to the formation of 2 mol of the desired 5- or 6-membered lactone. Attempts to form 7-membered lactones thus far only led to 14-membered macrodiolides instead. |
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Keywords: | Tandem metathesis Ring-closing metathesis Chiral pool Lactones Macrodiolides |
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