NOVEL POLYENE CYCLIZATION ROUTES TO THE ACYL TETRONIC ACID IONOPHORE TETRONASIN (ICI M139603)

被引：14

作者：

BOONS, GJ

LENNON, IC

LEY, SV

OWEN, ESE

STAUNTON, J

WADSWORTH, DJ

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

[2] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)76543-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the total synthesis of the ionophore antibiotic tetronasin (I) is reported, in which the key step is a novel base catalysed cascade cyslisation of an activated polyene (2). This establishes two rings and four stereogenic centres in one step. A related polyene (16) has been cyclised in a similar fashion, illustrating the generality of the procedure.

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页码：323 / 326

页数：4

相关论文

共 11 条

[1] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[2] IMPROVED CARBON-CARBON LINKING BY CONTROLLED COPPER CATALYSIS [J].

FOUQUET, G ;

SCHLOSSE.M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (01) :82-83

[3] DIANIONS OF BETA-KETO PHOSPHONATES - 2-STEP SYNTHESIS OF (+/-)-AR-TURMERONE [J].

GRIECO, PA ;

FINKELHO.RS .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (16) :2909-2910

[4] ALKYLATION OF DIANION OF BETA-KETO PHOSPHONATES - VERSATILE SYNTHESIS OF DIMETHYL (2-OXOALKYL)PHOSPHONATES [J].

GRIECO, PA ;

POGONOWSKI, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (09) :3071-3072

[5]

Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13

[6] PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].

GRIFFITH, WP ;

LEY, SV ;

WHITCOMBE, GP ;

WHITE, AD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627

[7] THE 1ST TOTAL SYNTHESIS OF TETRONASIN (M139603) [J].

HORI, K ;

KAZUNO, H ;

NOMURA, K ;

YOSHII, E .

TETRAHEDRON LETTERS, 1993, 34 (13) :2183-2186

[8] KNOEVENAGEL CONDENSATIONS WITH TICL4 BASE .4. REACTIONS OF ALDEHYDES AND KETONES WITH PHOSPHONOACETIC ESTER AND METHYLENEDIPHOSPHONATES [J].

LEHNERT, W .

TETRAHEDRON, 1974, 30 (02) :301-305

[9] ASYMMETRIC-SYNTHESIS VIA AXIALLY DISSYMMETRIC MOLECULES .6. RATIONAL DESIGNING OF EFFICIENT CHIRAL REDUCING AGENTS - HIGHLY ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES BY BINAPHTHOL-MODIFIED LITHIUM ALUMINUM-HYDRIDE REAGENTS [J].

NOYORI, R ;

TOMINO, I ;

TANIMOTO, Y ;

NISHIZAWA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6709-6716

[10]

NOYORI R, 1984, J AM CHEM SOC, V106, P6719