Synthesis of (-)-homogalanthamine from naltrexone

Naoshi Yamamoto; Hideaki Fujii; Satomi Imaide; Shigeto Hirayama; Toru Nemoto; Junji Inokoshi; Hiroshi Tomoda; Hiroshi Nagase

doi:10.1021/jo1022487

Synthesis of (-)-homogalanthamine from naltrexone

J Org Chem. 2011 Apr 1;76(7):2257-60. doi: 10.1021/jo1022487. Epub 2011 Mar 7.

Authors

Naoshi Yamamoto¹, Hideaki Fujii, Satomi Imaide, Shigeto Hirayama, Toru Nemoto, Junji Inokoshi, Hiroshi Tomoda, Hiroshi Nagase

Affiliation

¹ School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.

PMID: 21381712
DOI: 10.1021/jo1022487

Abstract

Acetylcholinesterase inhibitor (-)-homogalanthamine 3 was synthesized from μ opioid antagonist naltrexone (2) in 16% total yield. The synthesis features Grob fragmentation as a key reaction, which was especially accelerated in the presence of 15-crown-5.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crown Ethers / chemistry*
Galantamine / chemical synthesis*
Galantamine / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Naltrexone / chemical synthesis*
Naltrexone / chemistry*
Narcotic Antagonists / chemical synthesis*
Narcotic Antagonists / chemistry*
Receptors, Opioid, mu / antagonists & inhibitors*
Receptors, Opioid, mu / chemistry*

Substances

Crown Ethers
Narcotic Antagonists
Receptors, Opioid, mu
Galantamine
15-crown-5
Naltrexone