Total Synthesis of Pactamycin

被引：74

作者：

Hanessian, Stephen ^{[1
]}

Vakiti, Ramkrishna Reddy ^{[1
]}

Dorich, Stephane ^{[1
]}

Banerjee, Shyamapada ^{[1
]}

Lecomte, Fabien ^{[1
]}

DelValle, Juan R. ^{[1
]}

Zhang, Jianbin ^{[1
]}

Deschenes-Simard, Benoit ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Stn Ctr Ville, Montreal, PQ H3C 3J7, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

natural products; pactamycate; pactamycin; polysubstituted cyclopentanes; total synthesis; FORMAL TOTAL-SYNTHESIS; BIOSYNTHESIS; (+)-TREHAZOLIN; CYCLOPENTANE; INHIBITION; TREHAZOLIN; EFFICIENT;

D O I：

10.1002/anie.201008079

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lest we forget: 50 years after pactamycin was first isolated from a fermentation broth of Streptomyces pactum var pactum, this highly functionalized aminocyclopentitol natural product has finally succumbed to total synthesis. The modular and stereocontrolled introduction of functional groups should lead to the synthesis of less toxic congeners that maintain the antibacterial and cytotoxic activities. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3497 / 3500

页数：4

共 31 条

[1] DIRECTED BIOSYNTHESIS OF 5''-FLUOROPACTAMYCIN IN STREPTOMYCES-PACTUM
ADAMS, ES
RINEHART, KL
[J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (12) : 1456 - 1465
[2] Remarkably efficient charcoal-promoted ring-closing carbonylations
Alouane, N
Boutier, A
Baron, C
Vrancken, E
Mangeney, P
[J]. SYNTHESIS-STUTTGART, 2006, 5 (05): : 885 - 889
[3] Argoudelis A.D., 1962, ANTIMICROB AGENTS CH, P191
[4] Bhuyan B.K., 1962, Antimicrob. Agents Chemother, P184
[5] PACTAMYCIN AN ANTIBIOTIC THAT INHIBITS PROTEIN SYNTHESIS
BHUYAN, BK
[J]. BIOCHEMICAL PHARMACOLOGY, 1967, 16 (08) : 1411 - &
[6] Synthesis of trehazolin from D-glucose
Boiron, A
Zillig, P
Faber, D
Giese, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) : 5877 - 5882
[7] The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit
Brodersen, DE
Clemons, WM
Carter, AP
Morgan-Warren, RJ
Wimberly, BT
Ramakrishnan, V
[J]. CELL, 2000, 103 (07) : 1143 - 1154
[8] Asymmetric synthesis of the balanol heterocycle via a palladium-mediated epimerization and olefin metathesis
Cook, GR
Shanker, PS
Peterson, SL
[J]. ORGANIC LETTERS, 1999, 1 (04) : 615 - 617
[9] Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes
Crimmins, MT
Tabet, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) : 4012 - 4018
[10] de Gracia IS, 1998, J ORG CHEM, V63, P5883

← 1 2 3 4 →