New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium

被引：74

作者：

Morita, H

Hirasawa, Y

Shinzato, T

Kobayashi, J ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Univ Ryukyus, Fac Agr, Okinawa 9051427, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 33期

关键词：

alkaloids; phlegmarane; cernuane; quinolizidine;

D O I：

10.1016/j.tet.2003.09.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new phlegmarane-type alkaloids, cermizines A (1) and B (2), three new quinolizidine alkaloids, cermizine C (3) and senepodines G (4) and H (5), and a new C16N2 type alkaloid consisting of a quinolizidine and a piperidine ring, cermizine D (6), as well as two new cernuane-type alkaloids, cernuine N-oxide (7) and lycocernuine N-oxide (8), have been isolated together with cernuine (9) and lycocernuine (10) from the club moss Lycopodium cernuum and L. chinense. The relative stereochemistry of 1-4 and 6, and the absolute stereochemistry of 5, 7, and 8 were elucidated by combination of NOESY correlations, modified Mosher's method, chemical transformations, and computational methods. Cermizine D (6) might be a biosynthetic intermediate of cernuane-type alkaloids such as 7-10. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7015 / 7023

页数：9

共 36 条

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