A NEW APPROACH TO ARCHAEBACTERIAL LIPID MODELS

被引:15
作者
BERKOWITZ, WF
PAN, DF
BITTMAN, R
机构
[1] Department of Chemistry and Biochemistry, Queens College, the City University of New York, Flushing
关键词
D O I
10.1016/S0040-4039(00)79333-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,1'-(alpha,omega-Alkylidene)-2,2'-dialkylglycerol tetraether lipid models (9) have been prepared by coupling two equivalents of 1-(omega-haloalkyl)-2-alkylglycerol diethers, through silver-catalyzed coupling of the Grignard reagents 8 with iodide 7.
引用
收藏
页码:4297 / 4300
页数:4
相关论文
共 35 条
[11]  
ELFERINK MGL, 1992, J BIOL CHEM, V267, P1375
[12]   REGIOSPECIFIC OPENING OF GLYCIDYL DERIVATIVES MEDIATED BY BORON-TRIFLUORIDE - ASYMMETRIC-SYNTHESIS OF ETHER-LINKED PHOSPHOLIPIDS [J].
GUIVISDALSKY, PN ;
BITTMAN, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4637-4642
[13]   GLYCIDYL DERIVATIVES AS CHIRAL C-3 SYNTHONS - RING-OPENING CATALYZED BY BF3 ETHERATE [J].
GUIVISDALSKY, PN ;
BITTMAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :3077-3079
[14]  
GUIVISDALSKY PN, 1988, TETRAHEDRON LETT, V30, P4393
[15]   STEREOSTRUCTURE OF THE ARCHAEBACTERIAL C-40 DIOL [J].
HEATHCOCK, CH ;
FINKELSTEIN, BL ;
AOKI, T ;
POULTER, CD .
SCIENCE, 1985, 229 (4716) :862-864
[16]   ACYCLIC STEREOSELECTION .37. TOTAL SYNTHESIS OF A SLIGHTLY UNNATURAL PRODUCT - CONFIRMATION OF THE STEREOSTRUCTURE OF THE ARCHAEBACTERIAL-C40 DIOL BY SYNTHESIS OF A STEREOISOMER [J].
HEATHCOCK, CH ;
RADEL, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4322-4323
[17]   ACYCLIC STEREOSELECTION .42. 1,4-STEREOSELECTION AND 1,5-STEREOSELECTION BY SEQUENTIAL ALDOL ADDITION TO ALPHA,BETA-UNSATURATED ALDEHYDES FOLLOWED BY CLAISEN REARRANGEMENT - APPLICATION TO TOTAL SYNTHESIS OF THE VITAMIN-E SIDE-CHAIN AND THE ARCHAEBACTERIAL-C40 DIOL [J].
HEATHCOCK, CH ;
FINKELSTEIN, BL ;
JARVI, ET ;
RADEL, PA ;
HADLEY, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :1922-1942
[18]  
HUNIG S, 1973, ORG SYNTH, V5, P533
[19]   ACTIVE-SITE-DIRECTED SPECIFIC COMPETITIVE INHIBITORS OF PHOSPHOLIPASE-A2 - NOVEL TRANSITION-STATE ANALOGS [J].
JAIN, MK ;
TAO, WJ ;
ROGERS, J ;
ARENSON, C ;
EIBL, H ;
YU, BZ .
BIOCHEMISTRY, 1991, 30 (42) :10256-10268
[20]   TETRAETHER BOLAFORM AMPHIPHILES AS MODELS OF ARCHAEBACTERIAL MEMBRANE-LIPIDS - SYNTHESIS, DIFFERENTIAL SCANNING CALORIMETRY, AND MONOLAYER STUDIES [J].
KIM, JM ;
THOMPSON, DH .
LANGMUIR, 1992, 8 (02) :637-644