Exploitation of highly functionalised epoxides derived from asymmetrized tris(hydroxymethyl)methane (THYM*) in the synthesis of a fragment of lasalocide A and other related polyether ionofore antibiotics

被引：4

作者：

Guanti, G ^{[1
]}

Narisano, E ^{[1
]}

机构：

[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFAT & AROMAT,I-16146 GENOA,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 38期

关键词：

D O I：

10.1016/0040-4020(96)00751-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fragment for the total convergent synthesis of some polyether ionophore antibiotics (1a-salocide A, isolasalocide A, lysocellin) has been obtained through ''higher order'' vinyl cuprate ring opening of functionalised epoxides derived from THYM*. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：12631 / 12642

页数：12

共 22 条

[1] BORON FLUORIDE PROMOTED OPENING OF EPOXIDES BY ORGANOCOPPER AND CUPRATE REAGENTS [J].

ALEXAKIS, A ;

JACHIET, D ;

NORMANT, JF .

TETRAHEDRON, 1986, 42 (20) :5607-5619

[2] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN [J].

EVANS, DA ;

DOW, RL ;

SHIH, TL ;

TAKACS, JM ;

ZAHLER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5290-5313

[3] ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE AS A HIGHLY STEREODIVERGENT CHIRAL BUILDING BLOCK - PREPARATION OF ALL 4 STEREOISOMERS OF PROTECTED 2-HYDROXYMETHYL-1,3-BUTANEDIOL [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

TETRAHEDRON LETTERS, 1990, 31 (44) :6421-6424

[4] REGIOCONTROL IN NUCLEOPHILIC RING-OPENING OF CHIRAL EPOXIDES OF CHEMOENZYMATIC ORIGIN [J].

GUANTI, G ;

MERLO, V ;

NARISANO, E .

TETRAHEDRON, 1994, 50 (42) :12245-12258

[5] REGIOCONTROL IN REDUCTIVE RING-OPENING OF EPOXIDES DERIVED FROM ASYMMETRIZED 2-ALKENYL-1,3-PROPANEDIOLS [J].

GUANTI, G ;

BANFI, L ;

MERLO, V ;

NARISANO, E .

TETRAHEDRON, 1994, 50 (07) :2219-2230

[6] SYNTHESIS OF BOTH TOP AND BOTTOM FRAGMENTS OF (-)-TALAROMYCIN-A THROUGH ENANTIOSPECIFIC AND DIASTEREOSELECTIVE ELABORATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E ;

ZANNETTI, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1508-1514

[7] STEREODIVERGENT SYNTHESIS OF CIS EPOXIDES DERIVED FROM ASYMMETRIZED 2-ALKENYL-1,3-PROPANEDIOLS [J].

GUANTI, G ;

BANFI, L ;

MERLO, V ;

NARISANO, E ;

THEA, S .

TETRAHEDRON, 1993, 49 (42) :9501-9516

[8] CHEMOENZYMATIC PREPARATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE (THYM-STAR) AND OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-STAR) AS NEW HIGHLY VERSATILE CHIRAL BUILDING-BLOCKS [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1540-1554

[9]

GUANTI G, 1991, TETRAHEDRON LETT, V32, P6839

[10] STEREOSELECTIVE TOTAL SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS, ISOLASALOCID-A AND LASALOCID-A .1. STEREOCONTROLLED CONSTRUCTION OF THE C-RINGS (C-18-C-24) BY ACID-CATALYZED CYCLIZATION OF P-METHOXYPHENYLALLYL ALCOHOLS [J].

HORITA, K ;

NODA, I ;

TANAKA, K ;

MIURA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1993, 49 (27) :5979-5996

← 1 2 3 →