A NOVEL SYNTHETIC APPROACH TOWARD THE ZARAGOZIC ACIDS CORE STRUCTURE

被引：62

作者：

KOYAMA, H

BALL, RG

BERGER, GD

机构：

[1] Merck Research Laboratories Department of Basic Chemistry, Rahway, NJ 07065-0900

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 49期

关键词：

D O I：

10.1016/0040-4039(94)88460-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic approach toward the zaragozic acids core structure is described. New dipolarophiles in the 1,3-dipolar cycloaddition to the carbonyl ylides are reported. The substituent effect of the dipolarophiles is also discussed.

引用

页码：9185 / 9188

页数：4

共 33 条

[1] THE FIRST SYNTHESIS OF THE NOVEL 2,8-DIOXABICYCLO[3.2.1]OCTANE RING-SYSTEM - A KEY FEATURE OF THE SQUALESTATINS [J].

AGGARWAL, VK ;

WANG, MF ;

ZAPARUCHA, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :87-88

[2]

BAXTER A, 1992, J BIOL CHEM, V267, P11705

[3] ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE [J].

BERGSTROM, JD ;

KURTZ, MM ;

REW, DJ ;

AMEND, AM ;

KARKAS, JD ;

BOSTEDOR, RG ;

BANSAL, VS ;

DUFRESNE, C ;

VANMIDDLESWORTH, FL ;

HENSENS, OD ;

LIESCH, JM ;

ZINK, DL ;

WILSON, KE ;

ONISHI, J ;

MILLIGAN, JA ;

BILLS, G ;

KAPLAN, L ;

OMSTEAD, MN ;

JENKINS, RG ;

HUANG, L ;

MEINZ, MS ;

QUINN, L ;

BURG, RW ;

KONG, YL ;

MOCHALES, S ;

MOJENA, M ;

MARTIN, I ;

PELAEZ, F ;

DIEZ, MT ;

ALBERTS, AW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :80-84

[4]

BURK RM, 1993, TETRAHEDRON LETT, V34, P75

[5] DIESTERS OF ZARAGOZIC ACID-A - SYNTHESIS AND BIOLOGICAL-ACTIVITY [J].

CHIANG, YCP ;

BIFTU, T ;

DOSS, GA ;

PLEVYAK, SP ;

MARQUIS, RW ;

BERGSTROM, JD ;

KURTZ, MM ;

REW, DJ ;

BERGER, GD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) :2029-2034

[6]

DAWSON MJ, 1992, J ANTIBIOT, V45, P648

[7]

FLEMING I, 1976, FRONTIER ORBITALS OR

[8] REARRANGEMENT OF ZARAGOZIC ACID-A DERIVATIVES [J].

GIROTRA, NN ;

REAMER, RA ;

PONPIPOM, MM .

TETRAHEDRON LETTERS, 1993, 34 (27) :4293-4296

[9] THE ZARAGOZIC ACIDS - STRUCTURE ELUCIDATION OF A NEW CLASS OF SQUALENE SYNTHASE INHIBITORS [J].

HENSENS, OD ;

DUFRESNE, C ;

LIESCH, JM ;

ZINK, DL ;

REAMER, RA ;

VANMIDDLESWORTH, F .

TETRAHEDRON LETTERS, 1993, 34 (03) :399-402

[10] FRONTIER MOLECULAR-ORBITALS OF 1,3 DIPOLES AND DIPOLAROPHILES [J].

HOUK, KN ;

SIMS, J ;

DUKE, RE ;

STROZIER, RW ;

GEORGE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7287-7301

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