p-Vinyl phenyl containing alkaloid derivatives were copolymerized with divinylbenzene and the resulting insoluble macroporous polymers were treated with LiAlH(,4) to remove the accessible portion of the template alkaloids. N-Norreticuline was incorporated into the template cavities via a carbamate linkage. This polymer-bound N-norreticuline was treated with VOCl(,3) and upon removal of the product only isoboldine was isolated. / Oxidation of 3-oxoreticuline with phenyliodosodiacetate in the presence of trifluoroacetic acid gave 16-oxosalutaridine, 16-oxopallidine, 5-oxoisoboldine, and 6-oxothalidine in yields of 27%, 8%, 6%, and 10% respectively. Oxidation of 3-oxoreticuline with VOCl(,3) gave 16-oxopallidine, 5-oxoisoboldine, and 6-oxothalidine in 26%, 11%, and 9% yields respectively. Reduction of 16-oxosalutaridine with LiAlH(,4) gave salutaridinol, which was converted to ((+OR-))-thebaine upon treatment with dimethylformamide dineopentyl acetal. Since both salutaridinol and thebaine have been converted to codeine and morphine this work constitutes a formal total synthesis of these compounds. / Source: Dissertation Abstracts International, Volume: 45-11, Section: B, page: 3512. / Thesis (Ph.D.)--The Florida State University, 1984.
| Identifer | oai:union.ndltd.org:fsu.edu/oai:fsu.digital.flvc.org:fsu_75453 |
| Contributors | VANDERLAAN, DOUGLAS GEORGE., Florida State University |
| Source Sets | Florida State University |
| Detected Language | English |
| Type | Text |
| Format | 105 p. |
| Rights | On campus use only. |
| Relation | Dissertation Abstracts International |
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