An experimental and theoretical study of a bicyclic acetal equilibrium

被引：11

作者：

Dominey, AP ^{[1
]}

Goodman, JM ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol990669e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The position of equilibrium for competitive acetal formation can be hard to predict. This example, the core of zaragozic acid, is finely balanced, but an experimental investigation has proved that the left-hand isomer is preferred. Molecular mechanics force fields are unable to cope with such systems, because there is competition between five- and six-membered rings. Results from these calculations should not be used to estimate the position of equilibrium in such cases.

引用

页码：473 / 475

页数：3

共 22 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] Total synthesis of (+)-zaragozic acid C [J].

Armstrong, A ;

Jones, LH ;

Barsanti, PA .

TETRAHEDRON LETTERS, 1998, 39 (20) :3337-3340

[3]

ARMSTRONG A, 1995, SYNLETT, P903

[4] 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

[5] Total synthesis of zaragozic acid A (squalestatin S1). Synthesis of the relay compound [J].

Caron, S ;

Stoermer, D ;

Mapp, AK ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9126-9134

[6] SYNTHESIS OF 1-SUBSTITUTED AND 1,4-DISUBSTITUTED 2,3-DI-O-BENZYL-1,6-ANHYDROGALACTOFURANOSES [J].

CARON, S ;

MCDONALD, AI ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2780-2785

[7] (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8106-8125

[8] 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

[9] 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

[10] Short synthesis of the bicyclic core of the zaragozic acids [J].

Fraisse, P ;

Hanna, I ;

Lallemand, JY .

TETRAHEDRON LETTERS, 1998, 39 (43) :7853-7856

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