A NEW REGIOSELECTIVE SYNTHESIS OF ISOPAVINE AND PAVINE ALKALOIDS VIA DOUBLE CYCLIZATION OF ,2-DIARYLETHYL)-N-(2-PHENYLSULFINYLETHYL)FORMAMIDE

Authors
SHINOHARA T TAKEDA A TODA J SANO T
Citation
T. Shinohara et al., A NEW REGIOSELECTIVE SYNTHESIS OF ISOPAVINE AND PAVINE ALKALOIDS VIA DOUBLE CYCLIZATION OF ,2-DIARYLETHYL)-N-(2-PHENYLSULFINYLETHYL)FORMAMIDE, Heterocycles, 48(5), 1998, pp. 981-992
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
5
Year of publication
1998
Pages
981 - 992
Database
ISI
SICI code
0385-5414(1998)48:5<981:ANRSOI>2.0.ZU;2-Q
Abstract
Pummerer reaction of N-[l, 2-(3,4-dimethoxyphenyl)ethyl]-N- (2-phenyls ulfinylethyl)formamide (9) using trifluoroacetic anhydride and boron t rifluoride etherate caused double cyclization to give N-formylisopavin e (21.). Acid catalyzed cyclization of the 1,2-dihydroisoquinoline (23 ) prepared from 4-phenylthio-1,2,3,4-tetrahydroisoquinoline (11) gave N-formylpavine (26). LiAIH(4) reduction of the N-formates (21 and 26) gave (+/-)-O-methylthalisopavine (4) and (+/-)-argemonine (5), respect ively.