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Announcement
Yoshito Kishi (1937-2023)

Professor. Yoshito Kishi,
a member of the Honorary Editorial Associates of HETEROCYCLES,
has passed away on January 9, 2023 at the age of 85.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
January 13, 2023
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December 24, 2019
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■ A New Useful Conversion Method of Naltrexone to 14-Deoxynaltrexone
Yumiko Osa, Yoshihiro Ida, Yumiko Yano, Kimio Furuhata, and Hiroshi Nagase*
*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan
Abstract
A novel synthetic method of 14-deoxynaltrexone (2), a μ-opioid receptor antagonist possessing a new message-structural part of opioid ligands, was established. Naltrexone methyl ether (5) was first converted to its acetal (24), followed by dehydration with thionyl chloride in pyridine to afford 8,14-dehydroderivative (26) of 24. The resulting unsaturated compound (26) was reduced with PtO2 under hydrogen to give saturated compound (27), which was then acid-hydrolyzed to afford the desired 14-deoxynaltrexone (23) (3-O-methyl of 2) without degradation of the naltrexone skeleton. The total yield from naltrexone (1) to 23 was 86%. Finally, 23 was demethylated to give 14-deoxynaltrexone (2) in 85% yield. This method provides a useful reaction route to give various important intermediates as a message part to synthesize selective ligands for the opioid receptor subtypes.
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