SYNTHESIS OF VENTILAGONE

被引：6

作者：

CAMERON, DW

CROSBY, IT

FEUTRILL, GI

机构：

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1992年 / 45卷 / 12期

关键词：

D O I：

10.1071/CH9922025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of ventilagone (4) from the naphthol (5) was complicated by oxidation involving the central ring and by extensive epimerization to the trans series in the course of Lewis-acid-mediated demethylation. These complications were avoided by prior protection as the acetate (23). Oxidative demethylation and subsequent hydrolysis converted the latter into the dihydroxy quinone (6), which was also accessible from the nitro compound (26). Spectroscopic procedures for determining relative stereochemistry of such systems are discussed. Compound (6) underwent radical C-methylation to give ventilagone (4).

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页码：2025 / 2035

页数：11

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共 21 条

[1] NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS [J].

BECK, JR .

TETRAHEDRON, 1978, 34 (14) :2057-2068

[2] REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE FORMATION OF BENZISOCHROMAN-6,9-QUINONES - SYNTHESIS OF (+/-)-VENTILAGONE AND (+/-)-VENTILOQUINONE-H [J].

BLOUIN, M ;

BELAND, MC ;

BRASSARD, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1466-1471

[3] SYNTHESES OF KARWINAPHTHOL-B, 7-METHOXYELEUTHERIN AND VENTILOQUINONE-E [J].

CAMERON, DW ;

CROSBY, IT ;

FEUTRILL, GI ;

PIETERSZ, GA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (12) :2003-2024

[4] DIHYDROPYRAN DERIVATIVES FROM DIMERISATION OF CROTONALDEHYDE [J].

CAMERON, DW ;

SCHUTZ, PE .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (14) :1801-&

[5] COLORING MATTERS OF THE APHIDOIDEA .45. SYNTHESIS OF (+/-)-DEOXYQUINONE A DIMETHYL ETHER AND ITS EPIMER (+/-)-CIS-7,9-DIMETHOXY-1,3-DIMETHYL-3,4,5,10-TETRAHYDRO-1H-NAPHTHOL[2,3-C]PYRAN-5,10-DIONE [(+/-)-7-METHOXYELEUTHERIN] [J].

CAMERON, DW ;

FEUTRILL, GI ;

PIETERSZ, GA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (07) :1481-1487

[6] COLOURING MATTERS OF APHIDIDOE .22. NUCLEAR MAGNETIC RESONANCE EVIDENCE FOR STRUCTURES + CONFORMATIONS OF NAPHTHAQUINONE DIMETHYL ETHERS DERIVED FROM PROTOAPHINS + OF ERYTHROAPHINS [J].

CAMERON, DW ;

KINGSTON, DG ;

TODD ;

SHEPPARD, N .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JAN) :98-&

[7] NUCLEOPHILIC ALKENES .7. 1-2-ADDITION OF 1,1-DIMETHOXYETHENE TO 1,4-NAPHTHOQUINONES SUBSTITUTED IN THE BENZENOID RING [J].

CAMERON, DW ;

FEUTRILL, GI ;

PATTI, AF .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (08) :1805-1816

[8] COLOURING MATTERS OF AUSTRALIAN PLANTS .11. QUINONES FROM VENTILAGO VIMINALIS [J].

COOKE, RG ;

JOHNSON, BL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1963, 16 (04) :695-&

[9] COLORING MATTERS OF AUSTRALIAN PLANTS .22. VENTILAGONE - CRYSTAL-STRUCTURE AND AN APPROACH TO SYNTHESIS [J].

COOKE, RG ;

LIU, A ;

RASTON, CL ;

WHITE, AH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (02) :303-311

[10]

COOKE RG, 1965, B NAT I SCI INDIA, V28, P66