INTRAMOLECULAR PALLADIUM-CATALYZED CROSS COUPLING - A DIRECT ROUTE TO GAMMA-OXO-ALPHA,BETA-UNSATURATED MACROCYCLES

被引：32

作者：

BALDWIN, JE

ADLINGTON, RM

RAMCHARITAR, SH

机构：

[1] The Dyson Perrins Laboratory, University of Oxford, Oxford, OX1 3QY, South Parks Road

来源：

TETRAHEDRON | 1992年 / 48卷 / 14期

关键词：

STILLE MACROCYCLIZATION; GAMMA-OXO-ALPHA; BETA-UNSATURATED ESTERS; BETA-STANNYLALKENOATES; ANTIBIOTIC-A26771B; NORPATULOLIDE-B;

D O I：

10.1016/S0040-4020(01)90977-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Pd0-catalysed cross coupling of structures terminating in an acyl chloride and a beta-stannylalkenoate has provided a new and an efficient route to 10-20 membered gamma-oxo-alpha,beta-unsaturated macrolides. Both the Z- and E- beta-stannylalkenoates afforded identical macrocylic products demonstrating that under the reaction conditions thermodynamic equilibration of the first formed cross coupled product was most probably occurring. The method has been used to synthesise the macrocyclic framework of the antibiotic A26771B and norpatulolide B.

引用

页码：2957 / 2976

页数：20

共 36 条

[1] ASAOKA M, 1980, TETRAHEDRON LETT, P4611
[2] INTRAMOLECULAR PALLADIUM-CATALYZED CROSS COUPLING - A ROUTE TO GAMMA-OXO-ALPHA,BETA-UNSATURATED MACROCYCLES
BALDWIN, JE
ADLINGTON, RM
RAMCHARITAR, SH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) : 940 - 942
[3] 3,5-DISUBSTITUTED ISOXAZOLES AS SYNTHONS FOR (+/-)-PYRENOPHORIN AND (+/-)-VERMICULINE SYNTHESIS
BARALDI, PG
BARCO, A
BENETTI, S
MORODER, F
POLLINI, GP
SIMONI, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) : 1297 - 1302
[4] SYNTHESIS OF BETA-ACYLACRYLIC ESTERS AND ALPHA,BETA-BUTENOLIDES VIA BETA-KETO SULFOXIDE ALKYLATION
BARTLETT, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) : 3305 - 3312
[5] BEEBY PJ, 1977, TETRAHEDRON LETT, P3379
[6] OXIDATION OF ALPHA,BETA-UNSATURATED ESTERS AND LACTONES WITH SELENIUM DIOXIDE TO GAMMA-OXO OR GAMMA-HYDROXY DERIVATIVES - SYNTHESIS OF (+/-)-A 26771-B AND NORPYRENOPHORIN
BESTMANN, HJ
SCHOBERT, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1985, 24 (09) : 791 - 792
[7] REVISED STRUCTURE OF VERMICULINE - NOVEL MACROLIDE DILACTONE ANTIBIOTIC FROM PENICILLIUM-VERMICULATUM
BOECKMAN, RK
FAYOS, J
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (18) : 5954 - 5956
[8] TOTAL SYNTHESIS OF MACROCYCLIC ANTIBIOTIC (+ OR -)-PYRENOPHORIN
COLVIN, EW
PURCELL, TA
RAPHAEL, RA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (16): : 1718 - 1722
[9] 3-ALCOXY-ALLENYLLITHIUM REAGENTS AS BETA-ACYL VINYL ANION EQUIVALENTS - A NEW SYNTHESIS OF PYRENOPHORIN
DERGUINI, F
LINSTRUMELLE, G
[J]. TETRAHEDRON LETTERS, 1984, 25 (50) : 5763 - 5766
[10] RING-CLOSURE REACTIONS .14. KINETICS OF MACRO-CYCLIZATION BY THE INTRA-MOLECULAR ACYLATION OF THIOPHENE AND BENZOTHIOPHENE COMPOUNDS
GALLI, C
ILLUMINATI, G
MANDOLINI, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02) : 311 - 315

← 1 2 3 4 →