The structure of 8,11,15-trihydroxy-9,12-oxyeicosa-5,13-dienoic acid A, isolated by Pace-Asciak and Wolfe from enzymatic incubation of arachidonic acid, was proven by the synthesis of 8R,9S,11R,12S,15(R and S) isomers 1a and 1b. Both epimers were more polar than the natural product A. Reductive ozonolysis of 1a, followed by reaction of the resulting 2-acetoxyheptanal with l-ephedrine, gave oxazolidines whose R(,f) values on tlc were found to be characteristic of the chirality of the acetoxy group, thus permitting the determination of the absolute stereochemsitry at C-15 of 1a. / Model studies towards the synthesis of 9,11,15-trihydroxy-8,12-oxyeicosa-5,13-dienoic acid B were carried out.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68618 |
| Date | January 1981 |
| Creators | Oh, Hunseung, 1946- |
| 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: 000139958, proquestno: AAINK54881, Theses scanned by UMI/ProQuest. |
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