Solid-phase synthesis of polyamines using a Dde-linker: philanthotoxin-4.3.3 via an on-resin Mitsunobu reaction

被引：48

作者：

Chhabra, SR ^{[1
]}

Khan, AN ^{[1
]}

Bycroft, BW ^{[1
]}

机构：

[1] Univ Nottingham, Sch Pharmaceut Sci, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 07期

关键词：

solid-phase synthesis; polyamines; Mitsunobu reaction; Dde-linker;

D O I：

10.1016/S0040-4039(99)02239-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Dde linker/solid-phase procedure for the stepwise construction of polyamines is illustrated with the synthesis of philanthotoxin-4.3.3. Resin-bound 4-aza-1,7-heptanediamine was N-4-protected and N-7-activated in a single operation with 2-nitrobenzenesulphonyl chloride. Alkylation with N-Fmoc-4-aminobutanol under Mitsunobu conditions completed the polyamine backbone. Deprotection of the sulphonamide groups was readily achieved with thiolates in DMF at room temperature. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1099 / 1102

页数：4

共 16 条

[1] POLYAMINE AMIDE TOXINS AS PHARMACOLOGICAL TOOLS AND PHARMACEUTICAL AGENTS
BLAGBROUGH, IS
USHERWOOD, PNR
[J]. PROCEEDINGS OF THE ROYAL SOCIETY OF EDINBURGH SECTION B-BIOLOGICAL SCIENCES, 1992, 99 : 67 - 81
[2] Solid-phase synthesis of symmetrical and unsymmetrical polyamine analogues of philanthotoxins using a Dde-linker
Chhabra, SR
Khan, AN
Bycroft, BW
[J]. TETRAHEDRON LETTERS, 2000, 41 (07) : 1095 - 1098
[3] Versatile Dde-based primary amine linkers for solid phase synthesis
Chhabra, SR
Khan, AN
Bycroft, BW
[J]. TETRAHEDRON LETTERS, 1998, 39 (21) : 3585 - 3588
[4] USE OF THE MITSUNOBU REACTION IN THE SYNTHESIS OF POLYAMINES
EDWARDS, ML
STEMERICK, DM
MCCARTHY, JR
[J]. TETRAHEDRON, 1994, 50 (19) : 5579 - 5590
[5] STRUCTURE AND SYNTHESIS OF A POTENT GLUTAMATE RECEPTOR ANTAGONIST IN WASP VENOM
ELDEFRAWI, AT
ELDEFRAWI, ME
KONNO, K
MANSOUR, NA
NAKANISHI, K
OLTZ, E
USHERWOOD, PNR
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (13) : 4910 - 4913
[6] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES
FUKUYAMA, T
JOW, CK
CHEUNG, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (36) : 6373 - 6374
[7] SYNTHESIS OF GLUTAMATE RECEPTOR ANTAGONIST PHILANTHOTOXIN-433 (PHTX-433) AND ITS ANALOGS
GOODNOW, R
KONNO, K
NIWA, M
KALLIMOPOULOS, T
BUKOWNIK, R
LENARES, D
NAKANISHI, K
[J]. TETRAHEDRON, 1990, 46 (09) : 3267 - 3286
[8] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
HENRY, JR
MARCIN, LR
MCINTOSH, MC
SCOLA, PM
HARRIS, GD
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1989, 30 (42) : 5709 - 5712
[9] SYNTHESIS OF PHILANTHOTOXIN ANALOGS WITH A BRANCHED POLYAMINE MOIETY
KALIVRETENOS, AG
NAKANISHI, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) : 6596 - 6608
[10] Site-selective N-methylation of peptides on solid support
Miller, SC
Scanlan, TS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2301 - 2302

← 1 2 →