Stereoselective synthesis of (-)-cytoxazone

被引：35

作者：

Carda, M ^{[1
]}

González, F

Sánchez, R

Marco, JA

机构：

[1] Univ Jaume 1, Dept Quim Organ & Inorgan, E-12080 Castellon de La Plana, Spain

[2] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(02)00227-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective synthesis of the cytokine modulator (-)-cytoxazone in enantiopure form is described. Key steps of the process are a syn-stereoselective aldol addition of a chiral ketone mediated by chlorodicyclohexylborane, and a Curtius rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1005 / 1010

页数：6

共 26 条

[1] Aldol reactions with erythrulose derivatives:: Stereoselective synthesis of differentially protected syn-α,β-dihydroxy esters [J].

Carda, M ;

Murga, J ;

Falomir, E ;

González, F ;

Marco, JA .

TETRAHEDRON, 2000, 56 (04) :677-683

[2] An efficient preparation of silylated derivatives of L-erythrulose 3,4-O-acetals [J].

Carda, M ;

Rodríguez, S ;

Murga, J ;

Falomir, E ;

Marco, JA ;

Röper, H .

SYNTHETIC COMMUNICATIONS, 1999, 29 (15) :2601-2610

[3] Stereoselective synthesis of syn-α-methyl-β-hydroxy esters [J].

Carda, M ;

Murga, J ;

Falomir, E ;

González, F ;

Marco, JA .

TETRAHEDRON-ASYMMETRY, 2000, 11 (15) :3211-3220

[4] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[5] Synthesis of retinals fluorinated at odd-numbered side-chain positions and of the corresponding fluorobacteriorhodopsins [J].

Francesch, A ;

Alvarez, R ;

Lopez, S ;

deLera, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :310-319

[6] Asymmetric aldol route to hydroxyethylamine isostere: Stereoselective synthesis of the core unit of saquinavir [J].

Ghosh, AK ;

Hussain, KA ;

Fidanze, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6080-6082

[7] Applications of tin-containing intermediates to carbohydrate chemistry [J].

Grindley, TB .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 53, 1998, 53 :17-142

[8]

Hamersak Z, 2001, SYNTHESIS-STUTTGART, P1989

[9] Isolation and biological activity of a novel cytokine modulator, cytoxazone [J].

Kakeya, H ;

Morishita, M ;

Kobinata, K ;

Osono, M ;

Ishizuka, M ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1998, 51 (12) :1126-1128

[10] Cytoxazone:: A novel cytokine modulator containing a 2-oxazolidinone ring produced by Streptomyces sp. [J].

Kakeya, H ;

Morishita, M ;

Koshino, H ;

Morita, T ;

Kobayashi, K ;

Osada, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1052-1053

← 1 2 3 →