Favorskii-Type Rearrangement of the 4,5-Epoxymorphinan Skeleton

The aldol condensation of naltrexone with various aryl aldehydes gives the corresponding 7-benzylidenenaltrexone derivatives in high yields. However, novel C-ring-contracted morphinan compounds were produced when 2-pyridinecarboxaldehyde or its related analogues were used as a coupling partner. The...

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Published inOrganic letters Vol. 20; no. 6; pp. 1559 - 1562
Main Authors Kutsumura, Noriki, Koyama, Yasuaki, Suzuki, Yuko, Tominaga, Ken-ichi, Yamamoto, Naoshi, Saitoh, Tsuyoshi, Nagumo, Yasuyuki, Nagase, Hiroshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.03.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
7-BENZYLIDENENALTREXONE DERIVATIVES
REVERSER
CHRONIC SPINAL DOG
RECEPTOR ANTAGONISTS
STABLE CYCLOPROPANONE
RESISTANT PLASMODIUM-CHABAUDI
LEAD COMPOUND
MORPHINE-LIKE
PROPELLANES
NALORPHINE-LIKE DRUGS
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Summary:The aldol condensation of naltrexone with various aryl aldehydes gives the corresponding 7-benzylidenenaltrexone derivatives in high yields. However, novel C-ring-contracted morphinan compounds were produced when 2-pyridinecarboxaldehyde or its related analogues were used as a coupling partner. The key structural feature was the existence of the tetrahydrofuran ring (4,5-epoxy ring, E-ring) of the morphinan skeleton. The time-resolved in situ IR spectroscopy of the reaction system indicated the short-lived absorption of the distorted cyclopropanone intermediate.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00288