149777-72-0Relevant articles and documents
Total synthesis of 8,14-dihydromorphinandienone alkaloids
Ghavimi, Bahman,Magnus, Philip
, p. 1708 - 1711 (2014)
A collective synthesis of 8,14-dihydronorsalutaridine, 8,14- dihydrosalutaridine, norisosinomenine, and isosinomenine is reported. The strategy provides direct access to the correct oxidation level of the products. The combination of an organocatalyst guanidine superbase, a tertiary amine base, and a dehydrating agent was necessary for the successful Henry-Michael- dehydration cascade to form the phenanthrene motif. The required selective aliphatic nitro reduction could only be achieved under heterogeneous transfer-hydrogenation conditions.
THERAPEUTIC COMPOUNDS AND USES THEREOF
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Page/Page column 48; 58, (2019/07/17)
The present invention relates to compounds useful in the modulation of ion channel activity in cells. The invention also relates to use of these compounds in the treatment of pain, and pharmaceutical compositions containing these compounds and methods for their preparation.
Structural revision of the hancock alkaloid (-)-galipeine
Davies, Stephen G.,Fletcher, Ai M.,Houlsby, Ian T.T.,Roberts, Paul M.,Thomson, James E.
, p. 10673 - 10679 (2018/05/31)
The 1H and 13C NMR data of synthetic samples of (S)-N1-methyl-2- [2′-(3″-hydroxy-4″-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline, the originally proposed structure of the Hancock alkaloid (-)-galipeine, do not match those of the natural product. Herein, the preparation of the regioisomer (S)-N1-methyl-2-[2′- (3″-methoxy-4″-hydroxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline is reported, the 1H and 13C NMR data of which are in excellent agreement with those of (-)-galipeine. Comparison of specific rotation data enables assignment of the absolute (S)- configuration of the alkaloid, and together, these data engender the structural revision of (-)-galipeine to (S)-N1-methyl-2-[2′-(3″-methoxy-4″-hydroxyphenyl)ethyl]- 1,2,3,4-tetrahydroquinoline.