A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

被引：24

作者：

Mandville, G ^{[1
]}

Girard, C ^{[1
]}

Bloch, R ^{[1
]}

机构：

[1] UNIV PARIS 11,INST CHIM MOL ORSAY,CNRS,LAB CARBOCYCLES,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(97)00475-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

引用

页码：3665 / 3673

页数：9

共 25 条

[21] STEREOCONTROLLED SYNTHESIS OF CYCLIC ETHERS BY INTRAMOLECULAR HETERO-MICHAEL ADDITION .4. ENANTIOMERIC SYNTHESIS OF SUBSTITUTED AND FUSED OXEPANES [J].

SOLER, MA ;

PALAZON, JM ;

MARTIN, VS .

TETRAHEDRON LETTERS, 1993, 34 (34) :5471-5474

[22] SYNTHESES OF ENANTIOMERICALLY PURE TETRAHYDROFURAN BUILDING-BLOCKS FOR NACTIN AND PAMAMYCIN ANTIBIOTICS VIA AN ENZYMATICALLY RESOLVED GAMMA-HYDROXYALLENE [J].

WALKUP, RD ;

KIM, SW ;

WAGY, SD .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6486-6490

[23] SYNTHESIS OF THE C1'-C11' PORTION OF PAMAMYCIN-607 VIA A STEREOSELECTIVE OXYMERCURATION OF A GAMMA-SILYLOXYALLENE AND A STEREOSPECIFIC MAGNESIUM-METHANOL REDUCTION [J].

WALKUP, RD ;

PARK, G .

TETRAHEDRON LETTERS, 1988, 29 (43) :5505-5508

[24] SYNTHESIS OF A C-1-C-14 SUBUNIT OF THE MACRODIOLIDE ANTIBIOTICS PAMAMYCIN-607 AND PAMAMYCIN-635B [J].

WALKUP, RD ;

KIM, YS .

TETRAHEDRON LETTERS, 1995, 36 (18) :3091-3094

[25] SYNTHESES OF THE LOWER PORTIONS OF THE PAMAMYCINS FROM GAMMA-(SILYLOXY)ALLENES USING STEREOSELECTIVE CYCLIZATION, REDUCTION, AND ALDEHYDE ADDITION METHODOLOGIES [J].

WALKUP, RD ;

KIM, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3433-3441

← 1 2 3 →