Synthesis of didemnolines A-D, N9-substituted β-carboline alkaloids from the marine ascidian Didemnum sp.

被引：46

作者：

Schumacher, RW

Davidson, BS ^{[1
]}

机构：

[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA

[2] Utah State Univ, Dept Chem & Biochem, Logan, UT 84322 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 04期

关键词：

natural products; alkaloids; imidazoles;

D O I：

10.1016/S0040-4020(98)01100-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Didemnolines A-D (1-4) were synthesized and their structures were confirmed through comparisons of data for the synthetic material with those obtained for natural 1-4. The synthesis of didemnolines A (1) and C (3) involved the coupling of l-[(benzyloxy)methyl]-4-chloromethyl-5-(thiomethyl)imidazole (6) with 7-bromo-beta-carboline (5), while didemnolines B (2) and D (4) were formed through the analogous coupling of 6 with norharmon (7). Intermediate 6 was efficiently prepared from 1-[(benzyloxy)methyl]-2,4,5-tribromoimidazole using a sequential one-pot halogen-metal exchange reaction and 7-Br-beta-carboline was synthesized using a new approach (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：935 / 942

页数：8

共 31 条

[21] EUDISTOMINS C, E, K, AND L, POTENT ANTIVIRAL COMPOUNDS CONTAINING A NOVEL OXATHIAZEPINE RING FROM THE CARIBBEAN TUNICATE EUDISTOMA-OLIVACEUM [J].