Synlett

A novel approach to erythrinan alkaloids by utilizing substituted biphenyl as building block

Y Yasui, Y Koga, K Suzuki, T Matsumoto

Index: Yasui, Yoshizumi; Koga, Yukiko; Suzuki, Keisuke; Matsumoto, Takashi Synlett, 2004 , # 4 p. 615 - 618

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Citation Number: 17

Abstract

Abstract Aryl ortho-quinone monoacetal 6 possessing a carbamate group on the side chain was synthesized from the appropriate biphenyl precursor via selective oxidation of one of the aromatic rings. Under Lewis acidic conditions, the carbamate group underwent internal attack at the quinone acetal moiety to give the spiro tricycle 9 corresponding to the A-, C-, and D-rings of erythrinan alkaloids, from which O-methylerysodienone was synthesized ...