Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (-)-anisomycin and (+)-polyoxamic acid

被引：38

作者：

Kang, SH

Choi, HW

机构：

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 13期

关键词：

D O I：

10.1039/cc9960001521

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Intramolecular iodoamidation of pentenetriol 2 provides trihydroxy carbamate 8 in 94% de and was elaborated to (-)-anisomycin 15 and (+)-polyoxamic acid 19.

引用

页码：1521 / 1522

页数：2

共 30 条

[1] KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM [J].

ABIKO, A ;

ROBERTS, JC ;

TAKEMASA, T ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1986, 27 (38) :4537-4540

[2] STEREOSPECIFIC SYNTHESIS OF (-)-ANISOMYCIN FROM D-GALACTOSE [J].

BAER, HH ;

ZAMKANEI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4786-4789

[3] A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN [J].

BALLINI, R ;

MARCANTONI, E ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1316-1318

[4] STUDIES ON LACTAMS .89. VERSATILE BETA-LACTAM SYNTHONS - ENANTIOSPECIFIC SYNTHESIS OF (-)-POLYOXAMIC ACID [J].

BANIK, BK ;

MANHAS, MS ;

BOSE, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :307-309

[5] POLYOXIN-D INHIBITS GROWTH OF ZOOPATHOGENIC FUNGI [J].

BECKER, JM ;

COVERT, NL ;

SHENBAGAMURTHI, P ;

STEINFELD, AS ;

NAIDER, F .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1983, 23 (06) :926-929

[6] FACTORS AFFECTING THE REGIOSELECTION OF THE ALLYLIC IMIDATES IODOCYCLIZATION [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4905-4910

[7] A NEW SYNTHESIS OF (-)-ANISOMYCIN AND ITS DEMETHOXY ANALOG FROM D-RIBOSE [J].

BUCHANAN, JG ;

MACLEAN, KA ;

WIGHTMAN, RH ;

PAULSEN, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1463-1470

[8] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[9] TOTAL SYNTHESIS OF (+)-POLYOXIN-J STARTING FROM MYOINOSITOL [J].

CHIDA, N ;

KOIZUMI, K ;

KITADA, Y ;

YOKOYAMA, C ;

OGAWA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :111-113

[10]

DUREAULT A, 1991, SYNTHESIS-STUTTGART, P151

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