Isoquinoline compounds

Details Isoquinoline compounds Isoquinoline compounds

1974-05-08

1976-08-24

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D21720

Patent

active

039766527

ABSTRACT:
There is disclosed a novel total synthesis of Thalicarpine which includes inter alia a total synthesis of hernandaline. The novel process is characterized in utilizing simple and readily available starting materials to form a diaryl ether system which is then condensed with a 3,4-dihydroisoquinolinium salt which is then converted to hernandaline. Hernandaline is reacted with a bicyclic Reissert compound to yield a compound having the thalicarpine skeleton, nascent hydrogen reduction yields N-monodesmethyl thalicarpine which is methylated.

REFERENCES:
patent: 3117970 (1964-01-01), Weisbach
patent: 3717639 (1973-02-01), Neumeyer
Weisbach et al., "J. of Med. Chemistry", vol. 6, pp. 91-97 (1963).

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