STUDIES ON THE SYNTHESIS OF STEMONA ALKALOIDS - STEREOSELECTIVE PREPARATION OF THE HYDROINDOLE RING-SYSTEM BY OXIDATIVE CYCLIZATION OF TYROSINE

被引：126

作者：

WIPF, P

KIM, YT

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)61121-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The core hydroindole ring system of the Stemona alkaloids was prepared by oxidation of tyrosine with a hypervalent iodine reagent followed by a diastereotopic group-selective intramolecular conjugate addition. Further transformations illustrate the versatility of the highly functionalized hydroindolenone 3 for alkaloid synthesis.

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页码：5477 / 5480

页数：4

相关论文

共 38 条

[1] SELECTIVITY IN AN ASYMMETRIC NITROGEN INSERTION PROCESS [J].

AUBE, J ;

BURGETT, PM ;

WANG, Y .

TETRAHEDRON LETTERS, 1988, 29 (02) :151-154

[2] SYNTHESIS OF THE TRICYCLIC NUCLEUS OF THE ALKALOID STEMOFOLINE - X-RAY CRYSTAL-STRUCTURE OF (4RS,5RS,7SR,10RS)-10-BUTYL-5-HYDROXY-1-AZATRICYCLO[5.3.0.0(4,10)]DECAN-2-ONE [J].

BEDDOES, RL ;

DAVIES, MPH ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (07) :538-540

[3]

BURKERT U, 1982, ACS MONOGRAPH AM CHE, V177

[4] TOTAL SYNTHESIS OF DL-STENINE [J].

CHEN, CY ;

HART, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6236-6240

[5] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS [J].

DANGELO, J ;

MADDALUNO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8112-8114

[6] ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].

DAVIES, SG ;

ICHIHARA, O .

TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186

[7] CHIRAL RECOGNITION IN THE MICHAEL ADDITION-REACTION BETWEEN LITHIUM N-3,4-DIMETHOXYBENZYL-ALPHA-METHYLBENZYLAMIDE AND THE CHIRAL IRON CROTONOYL COMPLEX [(C5H5)FE(CO)(PPH3)(COCH=CHME)] [J].

DAVIES, SG ;

ICHIHARA, O .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) :1554-1555

[8] ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION DETERMINATION OF BETA-AMINO-GAMMA-BUTYROLACTONES AND AMINO DIOLS [J].

DELANGE, B ;

VANBOLHUIS, F ;

FERINGA, BL .

TETRAHEDRON, 1989, 45 (21) :6799-6818

[9] MODEL REACTION FOR BIOSYNTHESIS OF CRININ ALKALOIDS [J].

FRANCK, B ;

LUBS, HJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (03) :223-&

[10] ALKALOIDS OF AMARYLLIDACEAE .9. RACEMISATION OF BUPHANITINE (NERBOWDINE) DURING OPPENAUER OXIDATIONS [J].

GOOSEN, A ;

JOHN, EVO ;

YATES, KC ;

WARREN, FL .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (SEP) :4038-&

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