Efficient syntheses for appropriately derivatized methyl 8R,9(R and S), 11R-trihydroxy-12-oxododeca-5Z-enoates (53, 59) via their respective 5,6-anhydro-3-deoxy-1,2-0-isopropylidene-(alpha)-D-hexofuranoses (18 and 38) are described. These aldehydes were subsequently converted to the corresponding methyl 8(R and S), 9(R and S), 11R-trihydroxy-eicosa-5Z,12E,14Z-trienoates (64, 72, 82, 91). Model studies towards the synthesis of 8R,11R,15(R and S)-trihydroxy-9S,12-oxyeicosa-5Z,13E-dienoic acids (1) were carried out.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68571 |
| Date | January 1981 |
| Creators | Luthe, Corinne Elizabeth. |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 000114589, proquestno: AAINK52022, Theses scanned by UMI/ProQuest. |
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