Synthetic studies on the bryostatin B-ring
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| Title: | Synthetic studies on the bryostatin B-ring |
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| Authors: | Hummersone, Marc Geoffery |
| Summary: | A completely stereocontrolled asymmetric synthesis of an advanced B-ring synthon for the bryostatin family of antitumour agents is described in this thesis. Noteworthy features of our synthesis include the Smith-Tietze bis-alkylation reaction between 12 and 13 en route to C2-symmetrical ketone 10, and the totally stereoselective conversion of 10 into triol 18 via a Grignard addition tactic. Triol 18 was converted to epoxide 3 in nine steps and an acid-catalysed intramolecular Williamson etherification reaction completed the synthesis of 2. |
| URL: | https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.812685 |
| Database: | OpenDissertations |
| Abstract: | A completely stereocontrolled asymmetric synthesis of an advanced B-ring synthon for the bryostatin family of antitumour agents is described in this thesis. Noteworthy features of our synthesis include the Smith-Tietze bis-alkylation reaction between 12 and 13 en route to C2-symmetrical ketone 10, and the totally stereoselective conversion of 10 into triol 18 via a Grignard addition tactic. Triol 18 was converted to epoxide 3 in nine steps and an acid-catalysed intramolecular Williamson etherification reaction completed the synthesis of 2. |
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