Total synthesis of (+)-epopromycin B and its analogues - studies on the inhibition of cellulose biosynthesis

被引：10

作者：

Dobler, MR ^{[1
]}

机构：

[1] Novartis Crop Protect AG, Lead Discovery, CH-4002 Basel, Switzerland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)01944-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The described inhibition of the cellulose biosynthesis by epopromycin B prompted us to establish a short and efficient synthesis of the natural product, suitable for accessing a broad range of unnatural analogues in a multiparallel fashion. During the course of our synthesis the absolute configuration of (+)-epopromycin B could be determined. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：215 / 218

页数：4

共 10 条

[1] 1,2,2-tribromocyclopropanecarboxylic acid and derivatives - Valuable intermediates for four carbon cyclopropane and cyclopropene synthons
AlDulayymi, AR
AlDulayymi, JR
Baird, MS
Gerrard, ME
Koza, G
Harkins, SD
Roberts, E
[J]. TETRAHEDRON, 1996, 52 (10) : 3409 - 3424
[2] ISOLATION AND SYNTHESIS OF CAPROLACTIN-A AND CAPROLACTIN-B, NEW CAPROLACTAMS FROM A MARINE BACTERIUM
DAVIDSON, BS
SCHUMACHER, RW
[J]. TETRAHEDRON, 1993, 49 (30) : 6569 - 6574
[3] HATCH LF, 1950, J ORG CHEM, V15, P654
[4] A TOTAL SYNTHESIS OF 6,7-DIHYDROEPONEMYCIN AND DETERMINATION OF STEREOCHEMISTRY OF THE EPOXIDE RING
HOSHI, H
OHNUMA, T
ABURAKI, S
KONISHI, M
OKI, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (06) : 1047 - 1050
[5] NEW DIASTEREOSELECTIVE SYNTHESIS OF OXAZOLIDIN-2-ONES THROUGH CARBON CARBON BOND FORMATION ON CYCLIC CARBAMOYLOXY RADICALS
KANO, S
YOKOMATSU, T
SHIBUYA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) : 513 - 515
[6] TMC-86A, B and TMC-96, new proteasome inhibitors from Streptomyces sp TC 1084 and Saccharothrix sp TC 1094 -: I.: Taxonomy, fermentation, isolation, and biological activities
Koguchi, Y
Kohno, J
Suzuki, S
Nishio, M
Takahashi, K
Ohnuki, T
Komatsubara, S
[J]. JOURNAL OF ANTIBIOTICS, 1999, 52 (12) : 1069 - 1076
[7] THE SYNTHESIS OF EPONEMYCIN
SCHMIDT, U
SCHMIDT, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (07) : 529 - 530
[8] Eponemycin analogues: Syntheses and use as probes of angiogenesis
Sin, N
Meng, LH
Auth, H
Crews, CM
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (08) : 1209 - 1217
[9] EPONEMYCIN, A NEW ANTIBIOTIC ACTIVE AGAINST B16 MELANOMA .1. PRODUCTION, ISOLATION, STRUCTURE AND BIOLOGICAL-ACTIVITY
SUGAWARA, K
HATORI, M
NISHIYAMA, Y
TOMITA, K
KAMEI, H
KONISHI, M
OKI, T
[J]. JOURNAL OF ANTIBIOTICS, 1990, 43 (01) : 8 - 18
[10] Epopromycins, novel cell wall synthesis inhibitors of plant protoplast produced by Streptomyces sp. NK04000
Tsuchiya, K
Kobayashi, S
Nishikiori, T
Nakagawa, T
Tatsuta, K
[J]. JOURNAL OF ANTIBIOTICS, 1997, 50 (03) : 261 - 263

← 1 →