A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids

被引：50

作者：

Fresneda, PM ^{[1
]}

Molina, P ^{[1
]}

Sanz, MA ^{[1
]}

机构：

[1] Univ Murcia, Dept Quim Organ, Fac Quim, E-30071 Murcia, Spain

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 05期

关键词：

aza-Wittig reaction; natural products; sponges; nitrogen heterocycles;

D O I：

10.1016/S0040-4039(00)02120-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step synthesis of the N-acylated alpha -azido-omega -aminovalerate. a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding alpha -ureido ester derivative to give the 3-methylhydantoin ring present in midpacamide, whereas the reaction with triphenylphosphine. tosyl isocyanate and ammonia followed by cyclization of the resulting guanidine derivative provides the 2-aminoimidazole ring present in dispacamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：851 / 854

页数：4

共 24 条

[11] GRIBBLE GW, 1996, FORTSCHR CHEM ORG NA, V68, P137
[12] REACTION OF ARYLSULFONYL AZIDES WITH N-METHYLINDOLE
HARMON, RE
WELLMAN, G
GUPTA, SK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 11 - 16
[13] MAURITAMIDE-A AND ACCOMPANYING OROIDIN ALKALOIDS FROM THE SPONGE AGELAS-MAURITIANA
JIMENEZ, C
CREWS, P
[J]. TETRAHEDRON LETTERS, 1994, 35 (09) : 1375 - 1378
[14] Knowles H, 1997, SYNLETT, P271
[15] Application of ferrocenylalkyl chiral auxiliaries to syntheses of indolenine alkaloids:: Enantioselective syntheses of vincadifformine, ψ- and 20-epi-ψ-vincadifformines, tabersonine, ibophyllidine, and mossambine
Kuehne, ME
Bandarage, UK
Hammach, A
Li, YL
Wang, TS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2172 - 2183
[16] Lindel T, 1997, LIEBIGS ANN-RECL, P1525
[17] Synthesis of dispacamide from the marine sponge Agelas dispar
Lindel, T
Hoffmann, H
[J]. TETRAHEDRON LETTERS, 1997, 38 (52) : 8935 - 8938
[18] Synthesis of marine alkaloids isonaamine A, dorimidazole A, and preclathridine A.: Iminophosphorane-mediated preparation of 2-amino-1,4-disubstituted imidazoles from α-azido esters
Molina, P
Fresneda, PM
Sanz, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) : 2540 - 2544
[19] Synthesis of marine sponge alkaloids oroidin, clathrodin, and dispacamides. Preparation and transformation of 2-amino-4,5-dialkoxy-4,5-dihydroimidazolines from 2-aminoimidazoles
Olofson, A
Yakushijin, K
Horne, DA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 1248 - 1253
[20] Application of arene-ruthenium chemistry to a formal total synthesis of OF 4949 III
Pearson, AJ
Zhang, PL
Lee, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) : 6581 - 6586

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