Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 May 23;23(29):6993-6995.
doi: 10.1002/chem.201701438. Epub 2017 Apr 25.

Total Synthesis of (-)-Morphine

Hirotatsu Umihara  1 , Satoshi Yokoshima  2 , Masayuki Inoue  1 , Tohru Fukuyama  2
Affiliations

Total Synthesis of (-)-Morphine

Hirotatsu Umihara et al. Chemistry. .

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.

Keywords: aldol reaction; conjugate addition; morphine; singlet oxygen; total synthesis.

PubMed Disclaimer

LinkOut - more resources