Highly convergent three component benzyne coupling: the total synthesis of ent-clavilactone B |
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Authors: | Larrosa Igor Da Silva Marianne I Gómez Patricio M Hannen Peter Ko Eunjung Lenger Steven R Linke Simon R White Andrew J P Wilton Donna Barrett Anthony G M |
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Affiliation: | Department of Chemistry, Imperial College London, London SW7 2AZ, England. |
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Abstract: | The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B. |
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