N-Ethoxycarbonyl-5'-hydroxynorreticuline (1) was oxidized with vanadium oxytrichloride (VOCl(,3)) to give the para-ortho coupled N-ethoxycarbonyl-2-hydroxynorsalutaridine (2) in 55% yield. / Dienone 2 was converted into N-ethoxycarbonyl-2-hydroxynorthebaine (3) in 47% yield. Hydrolysis of 3 gave an 85% yield of N-ethoxycarbonyl-2-hydroxynorcodeinone (4) which upon reduction produced ((+OR-))-2-hydroxycodeine (5). / Reaction of the protected thebaine analogue 6 with singlet oxygen generated the protected 2,14-dihydroxynorcodeinone derivative 7. Selective dehydroxylation with concurrent double bond reduction gave the known N-ethoxycarbonylnoroxycodone (8); subsequent hydrolysis of 8 then concluded the total synthesis of ((+OR-))-noroxycodone (9). / Source: Dissertation Abstracts International, Volume: 42-01, Section: B, page: 0225. / Thesis (Ph.D.)--The Florida State University, 1981.
| Identifer | oai:union.ndltd.org:fsu.edu/oai:fsu.digital.flvc.org:fsu_74402 |
| Contributors | ZODA, MICHAEL FRANCIS., Florida State University |
| Source Sets | Florida State University |
| Detected Language | English |
| Type | Text |
| Format | 96 p. |
| Rights | On campus use only. |
| Relation | Dissertation Abstracts International |
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