Organic letters

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

…, Y Satoh, H Nishizawa, R Harada, M Tokuda

Index: Orito, Kazuhiko; Satoh, Yoshitaka; Nishizawa, Hidetoshi; Harada, Rika; Tokuda, Masao Organic Letters, 2000 , vol. 2, # 16 p. 2535 - 2537

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Citation Number: 35

Abstract

Treatment of 2-(2'-bromo-β-phenethyl) isocarbostyrils 7 with AIBN-Bu3SnH in boiling benzene gave 8-oxoberbines 3 in good yields. A similar treatment of 2-(2'-bromo-β- phenethyl) isoquinolinium bromides 6 and their nor-and homoanalogues (10, 11) induced 6- , 5-, and 7-exo radical closures in a one-pot manner to give protoberberines 2, dibenzo [b, g] indolizidine 14a and, dibenzo [a, h]-1-azabicyclo [5.4. 0] undecane 15a, respectively. A ...