An enantio- and stereocontrolled route to epopromycin B via cinchona alkaloid-catalyzed Baylis-Hillman reaction

被引：89

作者：

Iwabuchi, Y ^{[1
]}

Sugihara, T ^{[1
]}

Esumi, T ^{[1
]}

Hatakeyama, S ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 44期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(01)01676-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantio- and stereocontrolled route to epopromycin B having the epoxy-beta -aminoketone pharmacophore is developed based on the cinchona alkaloid-catalyzed Baylis-Hillman reaction of N-Fmoc-leucinal. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7867 / 7871

页数：5

共 22 条

[1] Ciganek E., 1997, ORG REACTIONS, V51, P201
[2] DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, P252
[3] Total synthesis of (+)-epopromycin B and its analogues - studies on the inhibition of cellulose biosynthesis
Dobler, MR
[J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 215 - 218
[4] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
PEDRINI, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1439 - 1446
[5] FACILE DIASTEREOSELECTIVE SYNTHESIS OF 2,6-DIALKYL-5-METHYLENE-1,3-DIOXAN-4-ONES VIA ALPHA-ACTIVATED VINYL ESTERS
DREWES, SE
EMSLIE, ND
KARODIA, N
KHAN, AA
[J]. CHEMISCHE BERICHTE, 1990, 123 (06) : 1447 - 1448
[6] Towards subunit-specific proteasome inhibitors:: synthesis and evaluation of peptide α′,β′-epoxyketones
Elofsson, M
Splittgerber, U
Myung, J
Mohan, R
Crews, CM
[J]. CHEMISTRY & BIOLOGY, 1999, 6 (11): : 811 - 822
[7] Crystal structure of epoxomicin:20S proteasome reveals a molecular basis for selectivity of α′,β′-epoxyketone proteasome inhibitors
Groll, M
Kim, KB
Kairies, N
Huber, R
Crews, CM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) : 1237 - 1238
[8] DABCO-CATALYZED COUPLING OF ALDEHYDES WITH ACTIVATED DOUBLE-BONDS .1. PREPARATION OF 2-(1-HYDROXYALKYL)ACRYLIC ESTERS - SIMPLE 3-STEP SYNTHESIS OF MIKANECIC ACID
HOFFMANN, HMR
RABE, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10): : 795 - 796
[9] 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
[10] Chiral amine-catalyzed asymmetric Baylis-Hillman reaction:: A reliable route to highly enantiomerically enriched (α-methylene-β-hydroxy)esters
Iwabuchi, Y
Nakatani, M
Yokoyama, N
Hatakeyama, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) : 10219 - 10220

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