The kinetics and thermodynamics of bicyclic ketal formation: An application to the synthesis of the zaragozic acids.

被引：15

作者：

Hegde, SG ^{[1
]}

Myles, DC ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90095

来源：

TETRAHEDRON | 1997年 / 53卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(97)00375-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：11179 / 11190

页数：12

共 17 条

[1]

ANTEUNIS MJO, 1976, HETEROCYCLES, V4, P293

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[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] DISCOVERY, BIOSYNTHESIS, AND MECHANISM OF ACTION OF THE ZARAGOZIC ACIDS - POTENT INHIBITORS OF SQUALENE SYNTHASE [J].

BERGSTROM, JD ;

DUFRESNE, C ;

BILLS, GF ;

NALLINOMSTEAD, M ;

BYRNE, K .

ANNUAL REVIEW OF MICROBIOLOGY, 1995, 49 :607-639

[5] SYNTHESIS OF (+)-ZARAGOZIC ACID-C [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10825-10826

[6] O,2-DILITHIO DERIVATIVE OF ALLYL ALCOHOL, A USEFUL SYNTHETIC REAGENT [J].

COREY, EJ ;

WIDIGER, GN .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (20) :2975-2976

[7] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY [J].

DAWSON, MJ ;

FARTHING, JE ;

MARSHALL, PS ;

MIDDLETON, RF ;

ONEILL, MJ ;

SHUTTLEWORTH, A ;

STYLLI, C ;

TAIT, RM ;

TAYLOR, PM ;

WILDMAN, HG ;

BUSS, AD ;

LANGLEY, D ;

HAYES, MV .

JOURNAL OF ANTIBIOTICS, 1992, 45 (05) :639-647

[8] THE ISOLATION AND STRUCTURE ELUCIDATION OF ZARAGOZIC ACID-C, A NOVEL POTENT SQUALENE SYNTHASE INHIBITOR [J].

DUFRESNE, C ;

WILSON, KE ;

ZINK, D ;

SMITH, J ;

BERGSTROM, JD ;

KURTZ, M ;

REW, D ;

NALLIN, M ;

JENKINS, R ;

BARTIZAL, K ;

TRAINOR, C ;

BILLS, G ;

MEINZ, M ;

HUANG, LY ;

ONISHI, J ;

MILLIGAN, J ;

MOJENA, M ;

PELAEZ, F .

TETRAHEDRON, 1992, 48 (47) :10221-10226

[9] CONFORMATIONAL ANALYSIS .16. 1,3-DIOXANES [J].

ELIEL, EL ;

KNOEBER, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) :3444-&

[10] ASYMMETRIC-SYNTHESIS OF THE SQUALENE SYNTHASE INHIBITOR ZARAGOZIC ACID-C [J].

EVANS, DA ;

BARROW, JC ;

LEIGHTON, JL ;

ROBICHAUD, AJ ;

SEFKOW, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12111-12112

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