A novel synthetic strategy for the potential analogue 17 of the immunosuppressive agents subglutinols A (3) and B ( 4) was investigated. Neither of these molecules, nor any analogues, have been synthesized previously. The route selected employed a cis -isopropylidene control group in the tether to facilitate the key synthetic step, an intramolecular Diels-Alder reaction. This approach afforded the tricyclic core of 18 in an efficient and direct manner. The Diels-Alder precursor 20 was constructed from D-isoascorbic acid (24), vinylmagnesium chloride (22), and 4-iodo-3-methoxymethoxymethyl-penta-1,3-diene (21). The synthesis of the lactone 19 and the attempts to remove the MOM group from 18 were also investigated. Unfortunately, however, the final target analogue 17 was not realized due to unsuccessful attempts at removing the MOM group from 18. Thus, an efficient route to the decalin core was established, though the coupling of the lactone 19 awaits further study.
| Identifer | oai:union.ndltd.org:uottawa.ca/oai:ruor.uottawa.ca:10393/9370 |
| Date | January 2001 |
| Creators | Ibrahim, Rana Hosni. |
| Contributors | Fallis, Alex G., |
| Publisher | University of Ottawa (Canada) |
| Source Sets | Université d’Ottawa |
| Detected Language | English |
| Type | Thesis |
| Format | 70 p. |
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