REGIOSPECIFIC PREPARATION OF CYCLOBUTENEDIONE MONOACETALS

被引:35
作者
LIEBESKIND, LS
WIRTZ, KR
机构
[1] Department of Chemistry, Emory University, Atlanta
关键词
D O I
10.1021/jo00306a011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 2,3-diisopropoxy-4-hydroxy-4-organyl-2-cyclobuten-l-ones, prepared by addition of nucleophiles (H-, C-sp3, C-sp2, C-sp) to diisopropyl squarate, with Me3SiOCH2CH2OSiMe3 and catalytic trimethylsilyl triflate in THF induces a regiospecific monoacetalization, providing the 3-isopropoxy-4-organyl-3-cyclobutene-l,2-dione 2-(ethylene acetal) in high yield. These compounds react with a wide range of nucleophiles to give 1,2-adducts that can be converted into 3,4-disubstituted-3-cyclobutene-l,2-dione-2-ethylene acetals under mild conditions. By changing the order of introduction of substituents, this sequence of reactions provides access to a variety of isomeric cyclobutenedione monoacetals in a regiodefined fashion. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:5350 / 5358
页数:9
相关论文
共 21 条
[1]   A BRIEF, CONVERGENT, REGIOSELECTIVE SYNTHESIS OF NAPHTHOQUINONES - A FORMAL SYNTHESIS OF NANAOMYCIN-A AND DEOXYFRENOLICIN [J].
DECKER, OHW ;
MOORE, HW .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1174-1175
[2]  
FENGL RW, 1990, J ORG CHEM, V55, P5359
[3]   REARRANGEMENT OF 4-ALKYNYLCYCLOBUTENONES - A NEW SYNTHESIS OF 1,4-BENZOQUINONES [J].
FOLAND, LD ;
KARLSSON, JO ;
PERRI, ST ;
SCHWABE, R ;
XU, SL ;
PATIL, S ;
MOORE, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :975-989
[4]   SYNTHESIS OF ISOARNEBIFURANONE, NANAOMYCIN, AND DEOXYFRENOLICIN - STRUCTURE ELUCIDATION OF ARNEBIFURANONE [J].
FOLAND, LD ;
DECKER, OHW ;
MOORE, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :989-995
[5]   (2-ALKYNYLETHENYL)KETENES - A NEW BENZOQUINONE SYNTHESIS [J].
KARLSSON, JO ;
NGUYEN, NV ;
FOLAND, LD ;
MOORE, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3392-3393
[6]   A STEREOSELECTIVE, PALLADIUM-CATALYZED ROUTE TO 4-OXYGENATED 5-ALKYLIDENECYCLOPENTENONES AND 3-OXYGENATED 2-ALKYLIDENEINDANONES [J].
LIEBESKIND, LS ;
MITCHELL, D ;
FOSTER, BS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7908-7910
[7]   A GENERAL, REGIOSPECIFIC SYNTHESIS OF HIGHLY SUBSTITUTED QUINONES [J].
LIEBESKIND, LS ;
IYER, S ;
JEWELL, CF .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3065-3067
[8]   CYCLOBUTENEDIONES AS PRECURSORS TO QUINONES AND CYCLOPENTENONES [J].
LIEBESKIND, LS .
TETRAHEDRON, 1989, 45 (10) :3053-3060
[9]   AN IMPROVED METHOD FOR THE SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES [J].
LIEBESKIND, LS ;
FENGL, RW ;
WIRTZ, KR ;
SHAWE, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2482-2488
[10]   (+/-)-BENZOABIKOVIROMYCIN, A POTENTIAL ANTIVIRAL AGENT SYNTHESIZED BY THE PALLADIUM-CATALYZED RING EXPANSION OF 2-ALKYNYL-2-HYDROXYBENZOCYCLOBUTENONES [J].
MITCHELL, D ;
LIEBESKIND, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :291-296