| Literature DB >> 28378531 |
Hirotatsu Umihara1, Satoshi Yokoshima2, Masayuki Inoue1, Tohru Fukuyama2.
Abstract
Asymmetric total synthesis of (-)-morphine has been accomplished in 18 steps from commercially available 7-methoxy-2-tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E-ring by acid-mediated cyclization, and singlet oxygen-mediated manipulation of the C-ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6-addition of in situ generated secondary amine.Entities:
Keywords: aldol reaction; conjugate addition; morphine; singlet oxygen; total synthesis
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Year: 2017 PMID: 28378531 DOI: 10.1002/chem.201701438
Source DB: PubMed Journal: Chemistry ISSN: 0947-6539 Impact factor: 5.236