Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B)

被引：70

作者：

Bhaket, P ^{[1
]}

Morris, K ^{[1
]}

Stauffer, CS ^{[1
]}

Datta, A ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol0473290

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from L-serine, a stereoselective synthesis of pachastrissamine, a structurally novel anhydrosphingosine derivative, is reported in this Letter.

引用

页码：875 / 876

页数：2

共 22 条

[1] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[2] Complex peptidyl nucleoside antibiotics: Efficient syntheses of the glycosyl nucleoside amino acid cores [J].

Bhaket, P ;

Stauffer, CS ;

Datta, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8594-8601

[3] Saturated oxygen heterocycles [J].

Elliott, MC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (21) :2301-2323

[4] NOVEL BIOACTIVE STYRYL-LACTONES - GONIOFUFURONE, GONIOPYPYRONE, AND 8-ACETYLGONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) - X-RAY MOLECULAR-STRUCTURE OF GONIOFUFURONE AND OF GONIOPYPYRONE [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

FANWICK, PE ;

MCLAUGHLIN, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1655-1661

[5]

GRACZA T, 1994, SYNTHESIS-STUTTGART, P1359

[6]

GRACZA T, 1991, SYNTHESIS-STUTTGART, P1108

[7] SYNTHESIS OF (1R,5R)-2,6-DIOXABICYCLO[3.3.0]OCTAN-3-ONE FROM D-GLUCOSE [J].

GURJAR, MK ;

PATIL, VJ ;

PAWAR, SM .

CARBOHYDRATE RESEARCH, 1987, 165 (02) :313-317

[8] SYNTHETIC ROUTES TO 2,5-DISUBSTITUTED TETRAHYDROFURANS [J].

HARMANGE, JC ;

FIGADERE, B .

TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1711-1754

[9] A SPIRO-BIS-GAMMA-LACTONE GLUCOSIDE FROM VIBURNUM-DILATATUM [J].

IWAGAWA, T ;

HASE, T .

PHYTOCHEMISTRY, 1984, 23 (10) :2299-2301

[10] Intramolecular cyclization of C-2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars [J].

Kang, SH ;

Ryu, DH .

TETRAHEDRON LETTERS, 1997, 38 (04) :607-610

← 1 2 3 →