Studies belated to the absolute configuration of cyclocinamide A:: Total synthesis of 4(R),11(R)-cyclocinamide A

被引：13

作者：

Grieco, PA ^{[1
]}

Reilly, M ^{[1
]}

机构：

[1] Montana State Univ, Dept Biochem & Chem, Bozeman, MT 59717 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(98)02016-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Coupling of the fluorenylmethyl ester 3 (R = Fm) of (S)-5-bromotryptophan with N-alpha-BOC-(S)-asn-O-benzoyl-(R)-ise 9 gave rise to tripeptide 10. Cleavage of the BOC group in 10 followed by coupling with N-alpha-BOC-N-beta-Fmoc-(R)-2,3-diamino-propanoic acid afforded tetrapeptide II which was transformed into cyclic peptide 12. Cleavage of the BOC in 12 followed by coupling with the glycine derived side chain 14 gave rise, after removal of the benzoyl group to 4(R),11(R)-cyclocinamide A (2) which was not identical to natural cyclocmamide A (1), suggesting that 1 possesses the 4(S),7(S),11(S),14(S) configuration, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8925 / 8928

页数：4

共 14 条

[1]

BEDNAREK MA, 1983, INT J PEPT PROT RES, V21, P196

[2]

CASTRO B, 1975, TETRAHEDRON LETT, P1219

[3] PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE - A NEW EFFICIENT COUPLING REAGENT IN PEPTIDE CHEMISTRY [J].

CHEN, SQ ;

XU, JC .

TETRAHEDRON LETTERS, 1991, 32 (46) :6711-6714

[4] Cyclocinamide A. An unusual cytotoxic halogenated hexapeptide from the marine sponge Psammocinia [J].

Clark, WD ;

Corbett, T ;

Valeriote, F ;

Crews, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9285-9286

[5] COMPARATIVE-STUDY OF SELECTED COUPLING REAGENTS IN DIPEPTIDE SYNTHESIS [J].

DUDASH, J ;

JIANG, JJ ;

MAYER, SC ;

JOULLIE, MM .

SYNTHETIC COMMUNICATIONS, 1993, 23 (03) :349-356

[6]

IRIE K, 1984, CHEM PHARM BULL, V32, P2126

[7] Total synthesis of dehydrodidemnin B. Use of uronium and phosphonium salt coupling reagents in peptide synthesis in solution [J].

Jou, G ;

Gonzalez, I ;

Albericio, F ;

LloydWilliams, P ;

Giralt, E .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :354-366

[8]

MATSUMOTO T, 1992, HETEROCYCLES, V34, P1697

[9]

MILEWSKA MJ, 1988, SYNTHESIS-STUTTGART, P475

[10]

NISHIWAKI E, 1988, HETEROCYCLES, V27, P1945

← 1 2 →