期刊
SYNLETT
卷 26, 期 15, 页码 2101-2108出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378808
关键词
photochemical oxidation; singlet oxygen; naltrexone synthesis; (R)-methylnaltrexone synthesis; N-demethylation of oripavine quaternary salts
资金
- Noramco, Inc.
- Natural Science and Engineering Council of Canada (NSERC) (Idea to Innovation and Discovery Grants)
- Canada Research Chair Program, Canada Foundation for Innovation (CFI)
- TDC Research, Inc.
- TDC Research Foundation
- Ontario Partnership for Innovation and Commercialization (OPIC)
- Advanced Biomanufacturing Centre (Brock University)
- University Centre of Excellence of Charles University, Prague, Czech Republic
(R)-Methylnaltrexone and naltrexone were each prepared in four steps from oripavine in practical yields. The procedure involved quaternization of oripavine with cyclopropylmethyl halides, singlet oxygen oxidation of the quaternary salts, and the reduction of endo peroxides to 14-hydroxyketone functionalities. (R)-Methylnaltrexone was prepared from the corresponding R-diastereomer of the oripavine salt. All diastereomeric mixtures of the quaternary salts were subjected to N-demethylation with sodium thiolate to yield cyclopropyl methylnororipavine, which was converted into naltrexone by peracid oxidation and hydrogenation according to established procedures.
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