Synthesis of a fully protected (2S,3R)-N-(1′,1′-dimethyl-2′-propenyl)-3-hydroxytryptophan from tryptophan

被引：17

作者：

Wen, SJ ^{[1
]}

Zhang, HW ^{[1
]}

Yao, ZJ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(02)01043-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S,3R)-N-(1',1'-Dimethyl-2'-propenyl)-3-hydroxytryptophan, a key amino acid of the anti-inflammatory cyclic peptide, cyclomarin C, has been synthesized stereoselectively, With full protection, from L-tryptophan for the first time. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5291 / 5294

页数：4

共 10 条

[1]

ARAI K, 1981, CHEM PHARM BULL, V29, P991

[2]

FUJINO M, 1964, CHEM PHARM BULL, V12, P1390

[3]

HAMADA Y, 1982, CHEM PHARM BULL, V30, P1921

[4] Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols [J].

Hoffman, RV ;

Maslouh, N ;

Cervantes-Lee, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1045-1056

[5] A REGIOCONTROLLED AND STEREOCONTROLLED TOTAL SYNTHESIS OF (-)-INDOLACTAM-V [J].

KOGAN, TP ;

SOMERS, TC ;

VENUTI, MC .

TETRAHEDRON, 1990, 46 (19) :6623-6632

[6] Indole alkaloids from a culture of the fungus Aporpium caryae [J].

Levy, LM ;

Cabrera, GM ;

Wright, JE ;

Seldes, AM .

PHYTOCHEMISTRY, 2000, 54 (08) :941-943

[7] Cyclomarins A-C, new antiinflammatory cyclic peptides produced by a marine bacterium (Streptomyces sp.) [J].

Renner, MK ;

Shen, YC ;

Cheng, XC ;

Jensen, PR ;

Frankmoelle, W ;

Kauffman, CA ;

Fenical, W ;

Lobkovsky, E ;

Clardy, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11273-11276

[8] Synthetic studies of N-reverse prenylated indole.: An efficient synthesis of antifungal indole alkaloids and N-reverse prenylated tryptophan [J].

Sugiyama, H ;

Yokokawa, F ;

Aoyama, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 2001, 42 (41) :7277-7280

[9]

Wen SJ, 2002, ACTA CHIM SINICA, V60, P129

[10]

YAMAMOTO Y, 1976, CHEM PHARM BULL, V24, P1853

← 1 →