Stereoselective synthesis of 4-amino-3-hydroxy-2-methylpentanoic acids: stereochemistry of the amino acid occurring in the marine toxin janolusimide

被引：6

作者：

Giordano, A ^{[1
]}

Spinella, A ^{[1
]}

Sodano, G ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, SA, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(99)00191-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Four diastereomers of 4-amino-3-hydroxy-2-methylpentanoic acid, an amino acid constituent of the hexapeptide portion of the antitumor antibiotic bleomycin A(2), have been stereoselectively synthesized by crotylboration of N-Boc-L-alaninal. The synthesis allowed the assignment of the stereochemistry as 2R,3S,4S to the 4-amino-3-hydroxy-2-methylpentanoic acid occurring in the tripeptide marine toxin janolusimide. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1851 / 1854

页数：4

共 20 条

[1] Definition of the effect and role of the bleomycin A2 valerate substituents:: Preorganization of a rigid, compact conformation implicated in sequence-selective DNA cleavage [J].

Boger, DL ;

Ramsey, TM ;

Cai, H ;

Hoehn, ST ;

Stubbe, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9149-9158

[2] A systematic evaluation of the bleomycin A2 L-threonine side chain:: Its role in preorganization of a compact conformation implicated in sequence-selective DNA cleavage [J].

Boger, DL ;

Ramsey, TM ;

Cai, H ;

Hoehn, ST ;

Stubbe, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9139-9148

[3] TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS [J].

BOGER, DL ;

COLLETTI, SL ;

HONDA, T ;

MENEZES, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5607-5618

[4] Assessment of the role of the bleomycin A2 pyrimidoblamic acid C4 amino group [J].

Boger, DL ;

Ramsey, TM ;

Cai, H ;

Hoehn, ST ;

Kozarich, JW ;

Stubbe, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :53-65

[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5919-5923

[6] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[7] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[8] (2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYLPENTANOIC ACID - ENANTIOSELECTIVE SYNTHESIS OF AN AMINO-ACID CONSTITUENT OF BLEOMYCIN [J].

DIPARDO, RM ;

BOCK, MG .

TETRAHEDRON LETTERS, 1983, 24 (44) :4805-4808

[9] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[10] A SYNTHESIS OF PROTECTED AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS [J].

LULY, JR ;

DELLARIA, JF ;

PLATTNER, JJ ;

SODERQUIST, JL ;

YI, N .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1487-1492

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