Enantioselective synthesis of the C10-C20 fragment of fusicoccin A |
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Authors: | Richter Anja Hedberg Christian Waldmann Herbert |
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Institution: | Fakult?t Chemie, Chemische Biologie, Technische Universit?t Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany. |
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Abstract: | A synthesis of the fully protected C-ring fragment of the tricyclic diterpene fusicoccin A is reported. The desired cyclopentenyl halides 5a,b are obtained in a total of nine steps. Key transformations of the synthesis sequence are a nonconventional Cr-catalyzed allylic oxidation of a protected intermediate cylcopentenone, a diastereoselective addition of a propenyl Grignard/CeCl(3) reagent to the unmasked cyclopentenone, and an asymmetric hydroboration of the isopropenyl substituent. The protected and suitably functionalized C-ring fragment paves the way to explore further the total synthesis of fusicoccin A. |
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