SYNTHESIS OF A C-1-C-14 SUBUNIT OF THE MACRODIOLIDE ANTIBIOTICS PAMAMYCIN-607 AND PAMAMYCIN-635B

被引：31

作者：

WALKUP, RD

KIM, YS

机构：

[1] Department of Chemistry and Biochemistry, Texas Tech University, Lubbock

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 18期

关键词：

D O I：

10.1016/0040-4039(95)00471-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nonracemic C-1-C-14 portion of the antibiotics pamamycin-607 and -635B was prepared using a route which features two stereoselective aldol reactions (including an apparent kinetic resolution via the Evans aldol reaction), a stereospecific intramolecular oxymercuration of a gamma-silyloxyallene, a stereospecific conjugate reduction of a beta-alkoxy-alpha-methylene carboxylate ester, and use of the 2,6-di-tert-butyl-4-methoxyphenyl ester group to ''protect'' a carboxylate function from reactions which normally occur at ester groups.

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收藏

页码：3091 / 3094

页数：4

相关论文

共 18 条

[1]

ABEL S, 1991, SYNLETT, P171

[2]

Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[3] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].

DANDA, H ;

HANSEN, MM ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181

[4] C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].

EVANS, DA ;

RIEGER, DL ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100

[5] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[6] NEW SYNTHETIC APPLICATIONS OF DIALKYLBORON HALIDE REAGENTS [J].

GUINDON, Y ;

ANDERSON, PC ;

YOAKIM, C ;

GIRARD, Y ;

BERTHIAUME, S ;

MORTON, HE .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1705-1714

[7] ACYCLIC STEREOSELECTION .13. ARYL ESTERS - REAGENTS FOR THREO-ALDOLIZATION [J].

HEATHCOCK, CH ;

PIRRUNG, MC ;

MONTGOMERY, SH ;

LAMPE, J .

TETRAHEDRON, 1981, 37 (23) :4087-4095

[8] ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE FROM STREPTOMYCES-ALBONIGER [J].

KONDO, S ;

YASUI, K ;

NATSUME, M ;

KATAYAMA, M ;

MARUMO, S .

JOURNAL OF ANTIBIOTICS, 1988, 41 (09) :1196-1204

[9] STRUCTURE OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE OF STREPTOMYCES-ALBONIGER [J].

KONDO, S ;

YASUI, K ;

KATAYAMA, M ;

MARUMO, S ;

KONDO, T ;

HATTORI, H .

TETRAHEDRON LETTERS, 1987, 28 (47) :5861-5864

[10] PAMAMYCIN - NEW ANTIBIOTIC AND STIMULATOR OF AERIAL MYCELIA FORMATION [J].

MCCANN, PA ;

POGELL, BM .

JOURNAL OF ANTIBIOTICS, 1979, 32 (07) :673-678