Hummersone, Marc Geoffery;
(2001)
Synthetic studies on the bryostatin B-ring.
Doctoral thesis (Ph.D), UCL (University College London).
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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.
| Type: | Thesis (Doctoral) |
|---|---|
| Qualification: | Ph.D |
| Title: | Synthetic studies on the bryostatin B-ring |
| Open access status: | An open access version is available from UCL Discovery |
| Language: | English |
| Additional information: | Thesis digitised by ProQuest. |
| Keywords: | Pure sciences; Health and environmental sciences; Antitumor agents |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10104654 |
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