The sugar-derived alkenes were prepared using three methods; in the first hex-5-enofuranoses were generated in good yields from the corresponding 5,6-dimesylates using Tipson-Cohen conditions; the second employed an aprotic Bamford-Stevens reaction to give the 1-methylene sugar from the analogous pyranosyl tosylhydrazone. The final approach gave a series of 1-methylene sugars in moderate to good yields (50-82%) by the methylation of sugar lactones with dimethyl titanocene (Petasis Reagent).
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:657082 |
| Date | January 2004 |
| Creators | McMillan, Keith G. |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/11147 |
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