Progress in the synthesis of the lituarines: stereocontrol in sequential C-C bond formation on a spirobutenolide template |
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Authors: | Robertson Jeremy Dallimore Jonathan W P |
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Affiliation: | Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK. jeremy.robertson@chem.ox.ac.uk |
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Abstract: | [structure: see text] We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core. |
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