Configuration of the psymberin amide side chain

被引：37

作者：

Kiren, S ^{[1
]}

Williams, LJ ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 14期

关键词：

D O I：

10.1021/ol0508375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structure of the amide side chain of psymberin, a potent and selective cytotoxin, is proposed. Syn and anti models of the amide side chain were prepared, and the structural assignment was confirmed by X-ray crystallographic analysis of the anti isomer. Comparison of H-1 and C-13 NMR data establishes homology between the natural product and the synthetic model compound of anti configuration and not the corresponding syn isomer.

引用

页码：2905 / 2908

页数：4

共 45 条

[31] Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products [J].

Matsumori, N ;

Kaneno, D ;

Murata, M ;

Nakamura, H ;

Tachibana, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :866-876

[32] METAL-ION CONTROLLED ADDITION TO ALPHA,BETA-DIALKOXY CARBONYL-COMPOUNDS [J].

MEAD, K ;

MACDONALD, TL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) :422-424

[33] ON THE STERIC COURSE OF THE ADDITION OF SOME ORGANOMETALLIC REAGENTS TO (R)-2,3-ISOPROPYLIDENE GLYCERALDEHYDE - SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-BENZYLOXY ALDEHYDES, ALCOHOLS, CARBOXYLIC-ACIDS AND 1,2-DIOLS [J].

MULZER, J ;

ANGERMANN, A .

TETRAHEDRON LETTERS, 1983, 24 (28) :2843-2846

[34]

Nazaré M, 2001, CHEM-EUR J, V7, P3363, DOI 10.1002/1521-3765(20010803)7:15<3363::AID-CHEM3363>3.0.CO

[35]

2-Y

[36] Antineoplastic agents.: 520.: Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa [J].

Pettit, GR ;

Xu, JP ;

Chapuis, JC ;

Pettit, RK ;

Tackett, LP ;

Doubek, DL ;

Hooper, JNA ;

Schmidt, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (05) :1149-1152

[37] Exploring the chemistry of uncultivated bacterial symbionts: Antitumor polyketides of the pederin family [J].

Piel, J ;

Butzke, D ;

Fusetani, N ;

Hui, DQ ;

Platzer, M ;

Wen, GP ;

Matsunaga, S .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (03) :472-479

[38] Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei [J].

Piel, J ;

Hui, DQ ;

Wen, GP ;

Butzke, D ;

Platzer, M ;

Fusetani, N ;

Matsunaga, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (46) :16222-16227

[39] CHELATION OR NON-CHELATION CONTROL IN ADDITION-REACTIONS OF CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY CARBONYL-COMPOUNDS [J].

REETZ, MT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :556-569

[40] SYNTHESIS OF 2,3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE IN HIGH CHEMICAL AND OPTICAL PURITY - OBSERVATIONS ON THE DEVELOPMENT OF A PRACTICAL BULK PROCESS [J].

SCHMID, CR ;

BRYANT, JD ;

DOWLATZEDAH, M ;

PHILLIPS, JL ;

PRATHER, DE ;

SCHANTZ, RD ;

SEAR, NL ;

VIANCO, CS .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4056-4058

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