Total synthesis of microsclerodermin E

被引:58
作者
Zhu, JD [1 ]
Ma, DW [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
amino acids; Julia reaction; macrocycles; pepticles; total synthesis;
D O I
10.1002/anie.200352423
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Succumbing to total synthesis: Microsclerodermin E, a 23-membered cyclic hexapeptide possessing antifungal activity, has been prepared for the first time. Key features in the synthesis include the construction of four unusual amino acid units, the assembly of the pyrrolidinone fragment with little racemization, and an effective macrocyclization.
引用
收藏
页码:5348 / 5351
页数:4
相关论文
共 29 条
[1]   A NEW, SHORT AND EFFICIENT SYNTHESIS OF BOTH ENANTIOMERS OF CARNITINE [J].
BELLAMY, FD ;
BONDOUX, M ;
DODEY, P .
TETRAHEDRON LETTERS, 1990, 31 (50) :7323-7326
[2]  
Bewley C. A., 1998, ANGEW CHEM, V110, P2280
[3]   MICROSCLERODERMIN-A AND MICROSCLERODERMIN-B - ANTIFUNGAL CYCLIC-PEPTIDES FROM THE LITHISTID SPONGE MICROSCLERODERMA SP [J].
BEWLEY, CA ;
DEBITUS, C ;
FAULKNER, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7631-7636
[4]   TOTAL SYNTHESIS OF OF4949-III AND OF4949-IV - UNUSUAL EFFECTS OF REMOTE SUBSTITUENTS ON THE RATE OF MACROCYCLIZATION REACTIONS [J].
BOGER, DL ;
YOHANNES, D .
TETRAHEDRON LETTERS, 1989, 30 (38) :5061-5064
[5]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[6]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[7]  
FEREZOU JP, 1995, B SOC CHIM FR, V132, P428
[8]  
FORST MP, 1992, J ORG CHEM, V57, P6671
[9]   A NEW METHOD FOR SYNTHESIS OF PEPTIDES - ACTIVATION OF CARBOXYL GROUP WITH DICYCLOHEXYLCARBODIIMIDE USING 1-HYDROXYBENZOTRIAZOLES AS ADDITIVES [J].
KONIG, W ;
GEIGER, R .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (03) :788-&
[10]  
Kudzin ZH, 1997, SYNTHESIS-STUTTGART, P44