Synthesis of the diazonamide A macrocyclic core via a Dieckmann-type cyclization

被引：35

作者：

Vedejs, E ^{[1
]}

Zajac, MA ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 16期

关键词：

D O I：

10.1021/ol016097r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Suzuki coupling of 18 and 30 affords 9 as an interconverting mixture of two atropisomers. Treatment with LDA at -23 degreesC affords the macrocyclic ketone 8 in 57% yield.

引用

页码：2451 / 2454

页数：4

共 36 条

[1] ADAM W, 1994, SYNTHESIS-STUTTGART, P111
[2] Studies towards the synthesis of diazonamide A. Synthesis of the 4-(oxazol-5-ylmethyl) aryltryptamine fragment
Bagley, MC
Moody, CJ
Pepper, AG
[J]. TETRAHEDRON LETTERS, 2000, 41 (35) : 6901 - 6904
[3] Studies towards the synthesis of diazonamide A. Synthesis of the indole bis-oxazole fragment
Bagley, MC
Hind, SL
Moody, CJ
[J]. TETRAHEDRON LETTERS, 2000, 41 (35) : 6897 - 6900
[4] 4-(DIMETHYLAMINO)PYRIDINE AS A CATALYST FOR CARBON ACYLATION .2. CONTROL OF CARBON VS OXYGEN ACYLATION IN BENZOFURANONES
BLACK, TH
ARRIVO, SM
SCHUMM, JS
KNOBELOCH, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) : 5425 - 5430
[5] A synthetic approach towards the aromatic macrocyclic core of diazonamide A based on sp2-sp2 coupling protocols
Boto, A
Ling, M
Meek, G
Pattenden, G
[J]. TETRAHEDRON LETTERS, 1998, 39 (44) : 8167 - 8170
[6] Synthesis of the 4-arylindole portion of the antitumor agent diazonamide and related studies
Chan, F
Magnus, P
McIver, EG
[J]. 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] Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus
Evans, DA
Cee, VJ
Smith, TE
Santiago, KJ
[J]. ORGANIC LETTERS, 1999, 1 (01) : 87 - 90
[10] Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: Approaches to diazonamide A
Fuerst, DE
Stoltz, BM
Wood, JL
[J]. ORGANIC LETTERS, 2000, 2 (22) : 3521 - 3523

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