Total synthesis and assignment of stereochemistry of raocyclamide cyclopeptides from cyanobacterium Oscillatoria raoi

被引：21

作者：

Freeman, DJ ^{[1
]}

Pattenden, G ^{[1
]}

机构：

[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(98)00404-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis demonstrates that the structures and stereochemistries of the cyclopeptides raocyclamide A and B isolated from a cyanobacterium should be altered to those shown in formulae 13 and 14 respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3251 / 3254

页数：4

共 15 条

[1] Raocyclamides A and B, novel cyclic hexapeptides isolated from the cyanobacterium Oscillatoria raoi [J].

Admi, V ;

Afek, U ;

Carmeli, S .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (04) :396-399

[2] TOTAL SYNTHESIS OF LISSOCLINAMIDE-5, A CYTOTOXIC CYCLIC PEPTIDE FROM THE TUNICATE LISSOCLINUM-PATELLA [J].

BODEN, C ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1994, 35 (44) :8271-8274

[3] CYCLOPEPTIDES FROM ASCIDIANS - TOTAL SYNTHESIS OF LISSOCLINAMIDE-4, AND A GENERAL STRATEGY FOR THE SYNTHESIS OF CHIRAL THIAZOLINE-CONTAINING MACROCYCLIC PEPTIDES [J].

BODEN, CDJ ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1995, 36 (34) :6153-6156

[4] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].

BURGESS, EM ;

PENTON, HR ;

TAYLOR, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31

[5]

BURGESS EM, 1988, ORG SYNTH, V6, P788

[6] NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

DEGNAN, BM ;

HAWKINS, CJ ;

LAVIN, MF ;

MCCAFFREY, EJ ;

PARRY, DL ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354

[7] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .67. A GENERAL-SYNTHESIS OF DERIVATIVES OF OPTICALLY PURE 2-(1-AMINOALKYL)THIAZOLE-4-CARBOXYLIC ACIDS [J].

HAMADA, Y ;

SHIBATA, M ;

SUGIURA, T ;

KATO, S ;

SHIOIRI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1252-1255

[8] CYCLOXAZOLINE - A CYTOTOXIC CYCLIC HEXAPEPTIDE FROM THE ASCIDIAN LISSOCLINUM-BISTRATUM [J].

HAMBLEY, TW ;

HAWKINS, CJ ;

LAVIN, MF ;

VANDENBRENK, A ;

WATTERS, DJ .

TETRAHEDRON, 1992, 48 (02) :341-348

[9] STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE LISSOCLINAMIDES - CYTOTOXIC CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

HAWKINS, CJ ;

LAVIN, MF ;

MARSHALL, KA ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1634-1638

[10] Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction [J].

Meyers, AI ;

Tavares, FX .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8207-8215

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