Studies towards the synthesis of diazonamide A. Synthesis of a tyrosine-derived benzofuranone

被引：43

作者：

Lach, F ^{[1
]}

Moody, CJ ^{[1
]}

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 35期

基金：

英国工程与自然科学研究理事会;

关键词：

Stille reaction; Claisen rearrangement; lactones;

D O I：

10.1016/S0040-4039(00)01118-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The benzofuranone 2, a potential intermediate for the synthesis of the marine natural product diazonamide A 1, has been synthesised in eight steps from the N-protected tyrosine eater 3, (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6893 / 6896

页数：4

共 26 条

[1] REGIOCONTROLLED AND STEREOCONTROLLED STANNYLMETALLATION OF 3,3-DIETHOXY-PROP-1-YNE AND 4,4-DIETHOXY-BUT-1-YNE - AN EFFICIENT ACCESS TO THE CORRESPONDING VINYLTINS WITH FIXED CONFIGURATIONS [J].

BEAUDET, I ;

PARRAIN, JL ;

QUINTARD, JP .

TETRAHEDRON LETTERS, 1991, 32 (44) :6333-6336

[2] An efficient method in stannylcupration of a methyl substituted enyne or alkyne by kinetic control using methanol [J].

Betzer, JF ;

Ardisson, J ;

Lallemand, JY ;

Pancrazi, A .

TETRAHEDRON LETTERS, 1997, 38 (13) :2279-2282

[3] 4-(DIMETHYLAMINO)PYRIDINE AS A CATALYST FOR CARBON ACYLATION .2. CONTROL OF CARBON VS OXYGEN ACYLATION IN BENZOFURANONES [J].

BLACK, TH ;

ARRIVO, SM ;

SCHUMM, JS ;

KNOBELOCH, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5425-5430

[4] SELECTIVELY PROTECTED L-DOPA DERIVATIVES - APPLICATION OF THE BENZYLIC HYDROPEROXIDE REARRANGEMENT [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5283-5286

[5] A synthetic approach towards the aromatic macrocyclic core of diazonamide A based on sp2-sp2 coupling protocols [J].

Boto, A ;

Ling, M ;

Meek, G ;

Pattenden, G .

TETRAHEDRON LETTERS, 1998, 39 (44) :8167-8170

[6] Synthesis of the 4-arylindole portion of the antitumor agent diazonamide and related studies [J].

Chan, F ;

Magnus, P ;

McIver, EG .

TETRAHEDRON LETTERS, 2000, 41 (06) :835-838

[7]

Chen X, 2000, ANGEW CHEM INT EDIT, V39, P937, DOI 10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO

[8]

2-A

[9] FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE [J].

CHEVALLET, P ;

GARROUSTE, P ;

MALAWSKA, B ;

MARTINEZ, J .

TETRAHEDRON LETTERS, 1993, 34 (46) :7409-7412

[10] Synthesis and SAR of diiodotyrosine-derived glycine-site N-methyl-D-aspartate receptor ligands [J].

Curtis, NR ;

Kulagowski, JJ ;

Leeson, PD ;

Mawer, IM ;

Ridgill, MP ;

Rowley, M ;

Grimwood, S ;

Marshall, GR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (10) :1145-1150

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