Determination of the relative and absolute configuration of the dimethylmyristoyl side chain of pneumocandin B0 by asymmetric synthesis

被引：11

作者：

Leonard, WR ^{[1
]}

Belyk, KM ^{[1
]}

Bender, DR ^{[1
]}

Conlon, DA ^{[1
]}

Hughes, DL ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 24期

关键词：

D O I：

10.1021/ol0261940

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative and absolute configuration of the pneumocandin B-0 side chain has been established as (10R,12S)-dimethylmyristoyl by the stereocontrolled synthesis of both antipodes of the side chain acid and their comparison to a sample derived from the natural product.

引用

页码：4201 / 4204

页数：4

共 21 条

[1] EVALUATION OF WATER-SOLUBLE PNEUMOCANDIN ANALOGS L-733560, L-705589, AND L-731373 WITH MOUSE MODELS OF DISSEMINATED ASPERGILLOSIS, CANDIDIASIS, AND CRYPTOCOCCOSIS [J].

ABRUZZO, GK ;

FLATTERY, AM ;

GILL, CJ ;

KONG, L ;

SMITH, JG ;

KRUPA, D ;

PIKOUNIS, VB ;

KROPP, H ;

BARTIZAL, K .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (05) :1077-1081

[2] Randomized, double-blind, Multicenter study of caspofungin versus amphotericin B for treatment of oropharyngeal and esophageal candidiases [J].

Arathoon, EG ;

Gotuzzo, E ;

Noriega, LM ;

Berman, RS ;

DiNubile, MJ ;

Sable, CA .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2002, 46 (02) :451-457

[3]

BALKOVEC JM, 1997, PHARMACOCHEM LIBR, V28, P1

[4] Reclassification of a pneumocandin-producing anamorph, Glarea lozoyensis gen. et sp. nov., previously identified as Zalerion arboricola [J].

Bills, GF ;

Platas, G ;

Peláez, F ;

Masurekar, P .

MYCOLOGICAL RESEARCH, 1999, 103 :179-192

[5] SYNTHESIS AND ANTIFUNGAL ACTIVITY OF NOVEL CATIONIC PNEUMOCANDIN B-O DERIVATIVES [J].

BOUFFARD, FA ;

ZAMBIAS, RA ;

DROPINSKI, JF ;

BALKOVEC, JM ;

HAMMOND, ML ;

ABRUZZO, GK ;

BARTIZAL, KF ;

MARRINAN, JA ;

KURTZ, MB ;

MCFADDEN, DC ;

NOLLSTADT, KH ;

POWLES, MA ;

SCHMATZ, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (02) :222-225

[6]

BOUFFARD FA, 1996, 36 INT C ANT AG CHEM, pF27

[7] REACTION OF ORGANOBORANES WITH 2-BROMOACROLEIN . A FACILE 1-STAGE SYNTHESIS OF ALPHA-BROMO ALDEHYDES [J].

BROWN, HC ;

KABALKA, GW ;

RATHKE, MW ;

ROGIC, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (15) :4165-&

[8]

DEBONO M, 1995, EXPERT OPIN THER PAT, V5, P771

[9] ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-HYDRAZONE RAMP-HYDRAZONE ENANTIOSELECTIVE SYNTHESIS OF PHEROMONES OF THE SMALL FOREST ANT (FORMICA-POLYCTENA) AND THE RED WOOD ANT (F-RUFA) [J].

ENDERS, D ;

RENDENBACH, BEM .

TETRAHEDRON, 1986, 42 (08) :2235-2242

[10]

Enders D., 1984, ASYMMETRIC SYNTHES B, V3, P275

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