Synthesis and stereochemical assignment of FR252921, a promising immunosuppressant

被引：33

作者：

Falck, J. Russell

He, Anyu

Fukui, Hiroki

Tsutsui, Hideyuki

Radha, Akella

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

[2] Univ Texas, SW Med Ctr, Dept Pharmacol, Dallas, TX 75390 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 24期

关键词：

configuration determination; immunosuppressants; macrocycles; natural products; total synthesis;

D O I：

10.1002/anie.200700321

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthetic detective work: FR252921, an unusual 19-membered lactone-dilactam, and three of its diastereomers were prepared by a versatile, convergent strategy from three key segments (see scheme). Comparison of the synthetic compounds with natural material established conclusively that FR252921 has the configuration 12S,13R,18R. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：4527 / 4529

页数：3

相关论文

共 24 条

[1]

Amans D., 2006, ANGEW CHEM, V118, P6002

[2] Total synthesis of pseudotrienic acid B:: A bioactive metabolite from Pseudomonas sp MF 381-IODS [J].

Amans, Dominique ;

Bellosta, Veronique ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5870-5874

[3] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].

COREY, EJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616

[4] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[5] FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens No. 408813 -: I.: Taxonomy, fermentation, isolation, physico-chemical properties and biological activities of FR252921, FR252922 and FR256523 [J].

Fujine, K ;

Tanaka, M ;

Ohsumi, K ;

Hashimoto, M ;

Takase, S ;

Ueda, H ;

Hino, M ;

Fujii, T .

JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :55-61

[6] FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens No. 408813 -: II.: In vitro property and mode of action [J].

Fujine, K ;

Abe, F ;

Seki, N ;

Ueda, H ;

Hino, M ;

Fujii, T .

JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :62-67

[7] FR252921, a novel immunosuppressive agent isolated from Pseudomona fluorescens No. 408813 -: III.: In vivo activities [J].

Fujine, K ;

Ueda, H ;

Hino, M ;

Fujii, T .

JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :68-71

[8] Asymmetric Samarium-Reformatsky reaction of chiral α-bromoacetyl-2-oxazolidinones with aldehydes [J].

Fukuzawa, S ;

Matsuzawa, H ;

Yoshimitsu, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1702-1706

[9] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[10] Reversal of stereoselectivity in the Evans aldol reaction of alpha,alpha-difluoro and alpha,alpha,alpha-trifluoro carbonyl compounds [J].

Iseki, K ;

Oishi, S ;

Kobayashi, Y .

TETRAHEDRON, 1996, 52 (01) :71-84