Synthetic studies towards the group A streptogramin antibiotics. Synthesis of the C9-C23 fragment

被引：35

作者：

Brennan, CJ ^{[1
]}

Campagne, JM ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(01)00973-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the C9-C23 subunit of the group A streptogramin antibiotics is described. The synthesis incorporates a palladium-catalysed sp-sp coupling and a catalytic asymmetric vinylogous Mukaiyama aldol reaction to induce the stereogenic centre at C14. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5195 / 5197

页数：3

共 40 条

[1] Anné S, 1999, SYNLETT, P1435
[2] Reactivity of 1-(Des-3-hydroxy-picolinoyl) pristinamycin IA
Barriére, JC
Bacqué, E
Puchault, G
Quenet, Y
Molherat, C
Cassayre, J
Paris, JM
[J]. TETRAHEDRON, 1998, 54 (42) : 12859 - 12886
[3] CUPRIC BROMIDE MEDIATED OXIDATION OF 4-CARBOXYOXAZOLINES TO THE CORRESPONDING OXAZOLES
BARRISH, JC
SINGH, J
SPERGEL, SH
HAN, WC
KISSICK, TP
KRONENTHAL, DR
MUELLER, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) : 4494 - 4496
[4] Exclusive gamma-regio functionalization of crotonaldehyde using gamma-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals.
Bellassoued, M
Salemkour, M
[J]. TETRAHEDRON, 1996, 52 (13) : 4607 - 4624
[5] SYNTHESIS OF THE OXAZOLE-CONTAINING AND DIENE-CONTAINING C9-C23 FRAGMENT OF THE TYPE-A STREPTOGRAMIN ANTIBIOTICS
BERGDAHL, M
HETT, R
FRIEBE, TL
GANGLOFF, AR
IQBAL, J
WU, YH
HELQUIST, P
[J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7371 - 7374
[6] Catalytic asymmetric vinylogous Mukaiyama (CAVM) reactions: aldehyde activation versus enolate activation
Bluet, G
Campagne, JM
[J]. TETRAHEDRON LETTERS, 1999, 40 (30) : 5507 - 5509
[7] Bluet G, 2000, SYNLETT, P221
[8] Breuilles P, 1998, TETRAHEDRON LETT, V39, P3149, DOI 10.1016/S0040-4039(98)00499-7
[9] Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes.: A short access to polyenaldehydes.
Cahard, D
Poirier, JM
Duhamel, P
[J]. TETRAHEDRON LETTERS, 1998, 39 (39) : 7093 - 7096
[10] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
Casiraghi, G
Zanardi, F
Appendino, G
Rassu, G
[J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1929 - 1972

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