SYNTHESIS OF THE OXINDOLE ALKALOID (-)-HORSFILINE

被引：100

作者：

PELLEGRINI, C ^{[1
]}

STRASSLER, C ^{[1
]}

WEBER, M ^{[1
]}

BORSCHBERG, HJ ^{[1
]}

机构：

[1] ETH ZENTRUM,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(00)86273-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-beta-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the unnatural optical antipode (+)-1, starting from 5-hydroxy-1-tryptophan as the single source from the chiral pool.

引用

页码：1979 / 1992

页数：14

共 25 条

[1]

AOYAMA T, 1984, CHEM PHARM BULL, V32, P3759

[2] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

TETRAHEDRON, 1985, 41 (19) :3901-3924

[3] MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1988, 44 (17) :5479-5486

[4]

BASCOP SI, 1994, HETEROCYCLES, V38, P725

[5]

BAXTER CAR, 1972, TETRAHEDRON LETT, V32, P3357

[6] STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED O-BROMOBENZAMIDES - ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES [J].

BELVISI, L ;

GENNARI, C ;

POLI, G ;

SCOLASTICO, C ;

SALOM, B .

TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :273-280

[7]

Bindra J. S, 1973, ALKALOIDS, V14, P83

[8]

BODANSZKY M, 1984, INT J PEPT PROT RES, V23, P565

[9] ALKALOIDS IN MAMMALIAN TISSUES .3. CONDENSATION OF L-TRYPTOPHAN AND L-5-HYDROXYTRYPTOPHAN WITH FORMALDEHYDE AND ACETALDEHYDE [J].

BROSSI, A ;

FOCELLA, A ;

TEITEL, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (04) :418-420

[10]

CALABRETTA R, 1991, SYNTHESIS-STUTTGART, P536

← 1 2 3 →