A SYNTHESIS OF (-)-TETRAHYDROLIPSTATIN IN WHICH THE RELATIVE STEREOCHEMISTRY IS CONTROLLED BY A PHENYLDIMETHYLSILYL GROUP

被引：67

作者：

FLEMING, I

LAWRENCE, NJ

机构：

[1] University Chemical Laboratory, Cambridge, CB2 1EW England, Lensfield Road

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)94466-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation ofa β-silylenolate and the hydroboration of an allylsilane successively control the relative stereochemistry of the three stereogenic centres on the carbon backbone in a synthesis of the esterase inhibitor tetrahydrolipstatin (21). © 1990.

引用

页码：3645 / 3648

页数：4

共 18 条

[1] STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES
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[2] STEREOSELECTIVE SYNTHESES OF TETRAHYDROLIPSTATIN AND OF AN ANALOG, POTENT PANCREATIC-LIPASE INHIBITORS CONTAINING A BETA-LACTONE MOIETY
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[3] SYNTHESES OF TETRAHYDROLIPSTATIN AND ABSOLUTE-CONFIGURATION OF TETRAHYDROLIPSTATIN AND LIPSTATIN
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SCHNEIDER, F
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (01) : 196 - 202
[4] BARBIER P, 1955, J ORG CHEM, V53, P1218
[5] STEREOCHEMISTRY IN THE HYDROBORATION OF ALLYLSILANES
FLEMING, I
LAWRENCE, NJ
[J]. TETRAHEDRON LETTERS, 1988, 29 (17) : 2077 - 2080
[6] DIASTEREOSELECTIVITY IN THE PREPARATION OF BETA-SILYLESTERS FROM ALPHA-BETA-UNSATURATED ESTERS AND AMIDES ATTACHED TO CHIRAL AUXILIARIES
FLEMING, I
KINDON, ND
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) : 1177 - 1179
[7] FLEMING I, 1986, J CHEM SOC CHEM COMM, P1199
[8] A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP
FLEMING, I
SANDERSON, PEJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (36) : 4229 - 4232
[9] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES
FLEMING, I
NEWTON, TW
ROESSLER, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2527 - 2532
[10] DIASTEREOSELECTIVITY IN THE ALKYLATION AND PROTONATION OF SOME BETA-SILYL ENOLATES
FLEMING, I
HILL, JHM
PARKER, D
WATERSON, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (06) : 318 - 321

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