Double benzyne-furan cycloaddition and the assembly of 1,1′-binaphthyl and 1,1′-dinaphthyl ether systems

被引:15
作者
Biland-Thommen, AS
Raju, GS
Blagg, J
White, AJP
Barrett, AGM [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] Pfizer Ltd, Global Res & Dev, Sandwich CT13 9NJ, Kent, England
基金
英国工程与自然科学研究理事会;
关键词
1,1 '-binaphthyl; 1,1 '-dinaphthyl ether; benzyne; cycloaddition; dibenzofuran;
D O I
10.1016/j.tetlet.2004.03.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,1'-Binaphthyl and 1,1'-dinaphthyl ether systems have been prepared via double benzyne-furan cycloadditions, and a dibenzofuran derivative was formed as a major product in the lithiation of two di-(chloroaryl) ethers. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:3181 / 3184
页数:4
相关论文
共 34 条
[11]   A NOVEL CLASS OF ANTITUMOR METABOLITES FROM THE FUNGUS NATTRASSIA-MANGIFERAE [J].
CHU, M ;
TRUUMEES, I ;
PATEL, MG ;
GULLO, VP ;
BLOOD, C ;
KING, I ;
PAI, JK ;
PUAR, MS .
TETRAHEDRON LETTERS, 1994, 35 (09) :1343-1346
[12]   Novel synthetic approaches to the palmarumycin skeleton [J].
Coutts, IGC ;
Allcock, RW ;
Scheeren, HW .
TETRAHEDRON LETTERS, 2000, 41 (47) :9105-9107
[13]   REGIOSELECTIVITY IN THE REACTIONS OF METHOXYDEHYDROBENZENES WITH FURANS .2. 2-METHOXYFURAN AND METHOXYDEHYDROBENZENES [J].
GILES, RGF ;
HUGHES, AB ;
SARGENT, MV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1581-1587
[14]   REGIOSELECTIVITY IN THE REACTIONS OF METHOXYDEHYDROBENZENES WITH FURANS .1. REACTIONS OF 3-METHOXYDEHYDROBENZENE AND 3-(METHOXYCARBONYL)-DEHYDROBENZENE WITH 2-SUBSTITUTED FURANS [J].
GILES, RGF ;
SARGENT, MV ;
SIANIPAR, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1571-1579
[15]   Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts [J].
Gujadhur, RK ;
Bates, CG ;
Venkataraman, D .
ORGANIC LETTERS, 2001, 3 (26) :4315-4317
[16]   General strategies for the synthesis of the major classes of C-aryl glycosides [J].
Kaelin, DE ;
Lopez, OD ;
Martin, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6937-6938
[17]   The absolute configuration of the palmarumycins C9, C10, and C12 by quantum-mechanical calculations of CD spectra [J].
Krohn, K ;
Steingröver, K ;
Zsila, F .
TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :1961-1964
[18]   Biologically active metabolites from fungi.: Part 16:: New preussomerins J, K and L from an endophytic fungus:: structure elucidation, crystal structure analysis and determination of absolute configuration by CD calculations [J].
Krohn, K ;
Flörke, U ;
John, M ;
Root, N ;
Steingröver, K ;
Aust, HJ ;
Draeger, S ;
Schulz, B ;
Antus, S ;
Simonyi, M ;
Zsila, F .
TETRAHEDRON, 2001, 57 (20) :4343-4348
[19]   Spiroxins, DNA cleaving antitumor antibiotics from a marine-derived fungus [J].
McDonald, LA ;
Abbanat, DR ;
Barbieri, LR ;
Bernan, VS ;
Discafani, CM ;
Greenstein, M ;
Janota, K ;
Korshalla, JD ;
Lassota, P ;
Tischler, M ;
Carter, GT .
TETRAHEDRON LETTERS, 1999, 40 (13) :2489-2492
[20]   Total synthesis of (±)-spiroxin C [J].
Miyashita, K ;
Sakai, T ;
Imanishi, T .
ORGANIC LETTERS, 2003, 5 (15) :2683-2686