Studies towards the synthesis of (+)-ptilomycalin A; Stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

被引：54

作者：

Louwrier, S ^{[1
]}

Ostendorf, M ^{[1
]}

Boom, A ^{[1
]}

Hiemstra, H ^{[1
]}

Speckamp, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM, ORGAN CHEM LAB, AMSTERDAM INST MOLEC STUDIES, 1018 WS AMSTERDAM, NETHERLANDS

来源：

TETRAHEDRON | 1996年 / 52卷 / 07期

关键词：

D O I：

10.1016/0040-4020(95)01085-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective N-acyliminium ion coupling reactions of beta-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.

引用

页码：2603 / 2628

页数：26

共 51 条

[41] A PRACTICAL AND DIVERGENT WAY TO TRIHYDROXYLATED PYRROLIDINE DERIVATIVES AS POTENTIAL GLYCOSIDASE INHIBITORS VIA STEREOSELECTIVE INTERMOLECULAR CIS-AMIDOALKYLATIONS [J].

RYU, Y ;

KIM, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :103-108

[42] ELECTROORGANIC CHEMISTRY .79. EFFICIENT SYNTHESIS OF PYRROLIZIDINE AND INDOLIZIDINE ALKALOIDS UTILIZING ANODICALLY PREPARED ALPHA-METHOXY CARBAMATES AS KEY INTERMEDIATES [J].

SHONO, T ;

MATSUMURA, Y ;

UCHIDA, K ;

TSUBATA, K ;

MAKINO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :300-304

[43] TOTAL SYNTHESIS OF THE LATRUNCULINS [J].

SMITH, AB ;

LEAHY, JW ;

NODA, I ;

REMISZEWSKI, SW ;

LIVERTON, NJ ;

ZIBUCK, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :2995-3007

[44] BIOMIMETIC SYNTHESIS OF THE CENTRAL TRICYCLIC PORTION OF PTILOMYCALIN-A [J].

SNIDER, BB ;

SHI, ZP .

TETRAHEDRON LETTERS, 1993, 34 (13) :2099-2102

[45] BIOMIMETIC SYNTHESIS OF THE PENTACYCLIC NUCLEUS OF PTILOMYCALIN-A [J].

SNIDER, BB ;

SHI, ZP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :549-557

[46] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].

STILL, WC ;

KAHN, M ;

MITRA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925

[47] SYNTHETIC APPLICATION OF ELECTROCHEMICALLY PRODUCED ALPHA-METHOXY AMIDES .3. ANODIC METHOXYLATION OF PYRROLIDINOL DERIVATIVES - ENANTIOSELECTIVE SYNTHESIS OF CIS-(3R)-3-HYDROXYPROLINES AND TRANS-(3R)-3-HYDROXYPROLINES [J].

THANING, M ;

WISTRAND, LG .

ACTA CHEMICA SCANDINAVICA, 1989, 43 (03) :290-295

[48] SYNTHETIC APPLICATIONS OF ELECTROCHEMICALLY PRODUCED ALPHA-METHOXY AMIDES .5. A SHORT ENANTIODIVERGENT SYNTHESIS OF THE GEISSMAN-WAISS LACTONE [J].

THANING, M ;

WISTRAND, LG .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1406-1408

[49] DIVERGENT, GENERALIZED SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED 2,5-PIPERAZINEDIONES [J].

WILLIAMS, RM ;

ARMSTRONG, RW ;

MARUYAMA, LK ;

DUNG, JS ;

ANDERSON, OP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3246-3253

[50] OXIDATIVE REMOVAL OF N-(4-METHOXYBENZYL) GROUP ON 2,5-PIPERAZINEDIONES WITH CERIUM(IV) DIAMMONIUM NITRATE [J].

YAMAURA, M ;

SUZUKI, T ;

HASHIMOTO, H ;

YOSHIMURA, J ;

OKAMOTO, T ;

SHIN, C .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (05) :1413-1420

← 1 2 3 4 5 6 →