On the verge of axial chirality: Atroposelective synthesis of the AB-biaryl fragment of vancomycin

被引：29

作者：

Bringmann, G

Menche, D

Muhlbacher, J

Reichert, M

Saito, N

Pfeiffer, SS

Lipshutz, BH

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol026182e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.

引用

页码：2833 / 2836

页数：4

共 38 条

[1] BEUGELMANS R, 1993, HETEROCYCLES, V36, P2723
[2] Bischoff D, 2001, ANGEW CHEM INT EDIT, V40, P4688, DOI 10.1002/1521-3773(20011217)40:24<4688::AID-ANIE4688>3.0.CO
[3] 2-M
[4] Diastereoselective total synthesis of the vancomycin aglycon with ordered atropisomer equilibrations
Boger, DL
Miyazaki, S
Kim, SH
Wu, JH
Loiseleur, O
Castle, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3226 - 3227
[5] Synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine derivatives: The central amino acid of vancomycin and related agents
Boger, DL
Borzilleri, RM
Nukui, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3561 - 3565
[6] Asymmetric synthesis of actinoidic acid derivatives
Boisnard, S
Neuville, L
Bois-Choussy, M
Zhu, JP
[J]. ORGANIC LETTERS, 2000, 2 (16) : 2459 - 2462
[7] Bringmann G, 2001, ANGEW CHEM INT EDIT, V40, P1687, DOI 10.1002/1521-3773(20010504)40:9<1687::AID-ANIE16870>3.3.CO
[8] 2-Y
[9] Stereoselective total synthesis of axially chiral natural products via biaryl lactones
Bringmann, G
Menche, D
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) : 615 - 624
[10] Nondynamic kinetic resolution of configurationally stable biaryl lactones by reduction with oxazaborolidine-activated borane: AM1 studies and experimental verification
Bringmann, G
Hinrichs, J
Kraus, J
Wuzik, A
Schulz, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) : 2517 - 2527

← 1 2 3 4 →