A synthetic approach towards the aromatic macrocyclic core of diazonamide A based on sp2-sp2 coupling protocols

被引：48

作者：

Boto, A ^{[1
]}

Ling, M ^{[1
]}

Meek, G ^{[1
]}

Pattenden, G ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 44期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)01819-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope for a range of sp(2)-sp(2) coupling protocols to elaborate the phenyl-indole, indole-oxazole, oxazole-oxazole, and quaternary carbon units in the marine natural product diazonamide A 1 are described, leading to the synthesis of the benzofuran oxazoles 11a and 18, the benzofuran/biphenyl/indole 16, and the indole-bis-oxazole 25. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8167 / 8170

页数：4

共 33 条

[11] The intramolecular Heck reaction
Gibson, SE
Middleton, RJ
[J]. CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (06): : 447 - 471
[12] PALLADIUM(II) CATALYZED CONSTRUCTION OF TETRASUBSTITUTED CARBON CENTERS, AND SPIRO-RING AND BRIDGED-RING COMPOUNDS FROM ENAMIDES OF 2-IODOBENZOIC ACIDS
GRIGG, R
SRIDHARAN, V
STEVENSON, P
WORAKUN, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) : 1697 - 1699
[13] Total synthesis of dimethyl sulfomycinamate
Kelly, TR
Lang, FR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4623 - 4633
[14] Konopelski JP, 1996, SYNLETT, P609
[15] SYNTHESIS OF BENZOFURANS VIA PALLADIUM-PROMOTED CYCLIZATION OF ORTHO-SUBSTITUTED ARYL ALLYL ETHERS
LAROCK, RC
STINN, DE
[J]. TETRAHEDRON LETTERS, 1988, 29 (37) : 4687 - 4690
[16] ISOLATION AND STRUCTURE DETERMINATION OF DIAZONAMIDE-A AND DIAZONAMIDE-B, UNUSUAL CYTOTOXIC METABOLITES FROM THE MARINE ASCIDIAN DIAZONA-CHINENSIS
LINDQUIST, N
FENICAL, W
VANDUYNE, GD
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) : 2303 - 2304
[17] CONTROLLING STEREOSELECTION IN INTRAMOLECULAR HECK REACTIONS BY TAILORING THE PALLADIUM CATALYST
MADIN, A
OVERMAN, LE
[J]. TETRAHEDRON LETTERS, 1992, 33 (34) : 4859 - 4862
[18] Muir JC, 1998, SYNTHESIS-STUTTGART, P613
[19] METAL-PROMOTED CYCLIZATION .22. SYNTHESIS OF BENZOFURANS, TETRAHYDROBENZOPYRANS, AND RELATED CYCLIC ETHERS VIA CYCLIC CARBOPALLADATION
NEGISHI, E
NGUYEN, T
OCONNOR, B
EVANS, JM
SILVEIRA, A
[J]. HETEROCYCLES, 1989, 28 (01) : 55 - 58
[20] REGIOSELECTIVE AND STEREOSELECTIVE FUNCTIONALIZATION OF AN OPTICALLY-ACTIVE TETRAHYDROINDOLIZINE DERIVATIVE - CATALYTIC ASYMMETRIC SYNTHESES OF LENTIGINOSINE, 1,2-DIEPILENTIGNOSINE, AND GEPHYROTOXIN-209D
NUKUI, S
SODEOKA, M
SASAI, H
SHIBASAKI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) : 398 - 404

← 1 2 3 4 →