Efficient asymmetric synthesis of (R)-3-hydroxy- and alkanoyloxytetradecanoic acids and method for the determination of enantiomeric purity

被引：29

作者：

Keegan, DS ^{[1
]}

Hagen, SR ^{[1
]}

Johnson, DA ^{[1
]}

机构：

[1] RIBI IMMUNOCHEM RES INC, DIV PHARMACEUT DISCOVERY, HAMILTON, MT 59840 USA

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(96)00464-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient synthesis of the (R)-3-hydroxy- and alkanoyloxytetradecanoic acid components of bacterial lipid A has been achieved using a Ru(II)-Binap-catalyzed low-pressure hydrogenation in the key step. The enantiomeric purity of p-bromophenacyl ester intermediate 4 could be assessed directly by chiral HPLC-obviating separate derivatization steps and/or chiral NMR shift studies. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：3559 / 3564

页数：6

共 18 条

[1] HIGHLY ENANTIOSELECTIVE HYDROGENATION OF BETA-KETO-ESTERS UNDER MILD CONDITIONS [J].

BURK, MJ ;

HARPER, TGP ;

KALBERG, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4423-4424

[2] TOTAL SYNTHESIS OF THE PROPOSED STRUCTURE OF RHODOBACTER-SPHAEROIDES LIPID-A RESULTING IN SYNTHESIS OF NEW POTENT LIPOPOLYSACCHARIDE ANTAGONISTS [J].

CHRIST, WJ ;

MCGUINNESS, PD ;

ASANO, O ;

WANG, Y ;

MULLARKEY, MA ;

PEREZ, M ;

HAWKINS, LD ;

BLYTHE, TA ;

DUBUC, GR ;

ROBIDOUX, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3637-3638

[3]

CHRIST WJ, 1993, Patent No. 536969

[4] PENTACYCLIC TRITERPENE SYNTHESIS .5. SYNTHESIS OF OPTICALLY PURE RING AB PRECURSORS [J].

DUTCHER, JS ;

MACMILLAN, JG ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (16) :2663-2669

[5] SYNTHESIS OF AN ANALOG OF BIOSYNTHETIC PRECURSOR IA OF LIPID-A BY AN IMPROVED METHOD - A NOVEL ANTAGONIST CONTAINING 4 (S)-3-HYDROXY FATTY-ACIDS [J].

FUKASE, K ;

LIU, WC ;

SUDA, Y ;

OIKAWA, M ;

WADA, A ;

MORI, S ;

ULMER, AJ ;

RIETSCHEL, ET ;

KUSUMOTO, S .

TETRAHEDRON LETTERS, 1995, 36 (41) :7455-7458

[6]

GENET JP, 1995, TETRAHEDRON LETT, V36, P4801

[7]

KAMIREDDY B, 1993, Patent No. 19761

[8] AN IMPROVED PROCEDURE FOR THE SYNTHESIS AND USE OF [RUCL2(BINAP)]2.NET3 - DEPENDENCE OF THE RU(II)-BINAP CATALYZED ASYMMETRIC HYDROGENATION OF BETA-KETO-ESTERS ON TRACE AMOUNTS OF ACID [J].

KING, SA ;

THOMPSON, AS ;

KING, AO ;

VERHOEVEN, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6689-6691

[9] SYNTHESIS OF NONREDUCING-SUGAR SUBUNIT ANALOGS OF BACTERIAL LIPID A CARRYING AN AMIDE-BOUND (3R)-3-ACYLOXY-TETRADECANOYL GROUP [J].

KISO, M ;

TANAKA, S ;

FUJITA, M ;

FUJISHIMA, Y ;

OGAWA, Y ;

HASEGAWA, A .

CARBOHYDRATE RESEARCH, 1987, 162 (02) :247-256

[10] CONVENIENT PREPARATION OF BINAP RUTHENIUM(II) COMPLEXES CATALYZING ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES [J].

KITAMURA, M ;

TOKUNAGA, M ;

OHKUMA, T ;

NOYORI, R .

TETRAHEDRON LETTERS, 1991, 32 (33) :4163-4166

← 1 2 →