Total synthesis of the marine alkaloid halitulin

被引：41
|
作者：
Heinrich, MR
Steglich, W
Banwell, MG
Kashman, Y
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
[3] Tel Aviv Univ, Sch Chem, IL-69978 Tel Aviv, Israel
来源：
TETRAHEDRON | 2003年 / 59卷 / 46期
关键词：
natural product synthesis; marine metabolites; halitulin; quinoline-7,8-diols; Baeyer-Villiger oxidation; Suzuki reaction;
D O I：
10.1016/j.tet.2003.02.005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9239 / 9247
页数：9
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