Synthesis and absolute configuration of axially chiral binaphthoquinones

被引：19

作者：

Baker, RW ^{[1
]}

Liu, S ^{[1
]}

Sargent, MV ^{[1
]}

机构：

[1] Univ Western Australia, Dept Chem, Nedlands, WA 6907, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1998年 / 51卷 / 04期

关键词：

D O I：

10.1071/C97088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of (+)-(S)-1',4-dihydroxy-2,3'-dimethyl-1,2'-binaphthalene-5,5',8,8'-tetrone (62) and (+)-(S)-4,5',8'-trihydroxy-2,3'-dimethyl-1,2'-binaphthalene-1',4',5,8-tetrone (55), compounds which are atropisomeric with the naturally occurring binaphthoquinones (-)-isodiospyrin and (-)-8'-hydroxyisodiospyrin, respectively, is described. The binaphthyl linkages in these compounds were stereoselectively constructed by using oxazoline chemistry. The stereochemical assignments were based on X-ray crystal structure determination and circular dichroic spectroscopy.

引用

页码：255 / 266

页数：12

共 34 条

[1]

ALVES AC, 1973, AN FAC FARM PORTO, V33, P5

[2] Absolute stereochemistry of 1,2'-linked bi(naphthoquinone)s [J].

Baker, RW ;

Liu, S ;

Sargent, MV ;

Skelton, BW ;

White, AH .

CHEMICAL COMMUNICATIONS, 1997, (05) :451-452

[3] Regioselectivity in the lithiation of 1,3-disubstituted arenes [J].

Baker, RW ;

Liu, S ;

Sargent, MV ;

Skelton, BW ;

White, AH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (08) :831-840

[4] Convergent synthesis of naphthylisoquinoline alkaloids: Total synthesis of (+)-O-methylancistrocline [J].

Chau, P ;

Czuba, IR ;

Rizzacasa, MA ;

Bringmann, G ;

Gulden, KP ;

Schaffer, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7101-7105

[5] SYNTHESIS OF LARREANTIN, A CYTOTOXIC NAPHTHOQUINONOID SESQUILIGNAN FROM LARREA-TRIDENTATA [J].

COMBER, MF ;

SARGENT, MV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2783-2787

[6] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[7]

FALLAS AL, 1968, J CHEM SOC C, P2879

[8] NAPHTHOQUINONES FROM EUCLEA-PSEUDEBENUS [J].

FERREIRA, MA ;

AUREACRU.M ;

CORREIAA.A ;

LOPES, MH .

PHYTOCHEMISTRY, 1974, 13 (08) :1587-1589

[9] NAPHTHOQUINONE DIMERS AND TRIMERS FROM EUCLEA-NATALENSIS [J].

FERREIRA, MA ;

CORREIAALVES, A ;

AUREACRUZCOSTA, M ;

ISABELPAUL, M .

PHYTOCHEMISTRY, 1977, 16 (01) :117-120

[10] A synthetic approach to (+)-dioncophylline C [J].

Gable, RW ;

Martin, RL ;

Rizzacasa, MA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (12) :2013-2021

← 1 2 3 4 →