SYNTHESES OF KARWINAPHTHOL-B, 7-METHOXYELEUTHERIN AND VENTILOQUINONE-E

被引:11
作者
CAMERON, DW
CROSBY, IT
FEUTRILL, GI
PIETERSZ, GA
机构
关键词
D O I
10.1071/CH9922003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Acylation of the aryl nitromethane (35) with (9) gave the enone (45), which underwent cyclization to the tricyclic system (50). Thermally induced aromatization to the naphthopyran (51) and oxidation gave ventiloquinone E (3). On selective demethylation this gave ventiloquinone G methyl ether (54). Analogous chemistry based on the aryl nitromethane (57) gave tricyclic nitro compound (60). On thermally induced aromatization this gave karwinaphthol B (5), while application of the Nef reaction and concomitant oxidation gave 7-methoxyeleutherin (2).
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页码:2003 / 2024
页数:22
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共 42 条
[1]   REACTIONS OF SOME ORTHO NAPHTHOQUINONES WITH 2,3-DIMETHYLBUTADIENE [J].
ANSELL, MF ;
MURRAY, RA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08) :1429-&
[2]   FORMATION OF SOME LINEAR POLYCYCLIC DIQUINONES VIA A NOVEL DIMERIZATION [J].
BAXTER, I ;
CAMERON, DW ;
TITMAN, RB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (07) :1253-&
[3]   KALAFUNGIN A NEW BROAD SPECTRUM ANTIBIOTIC - ISOLATION AND CHARACTERIZATION [J].
BERGY, ME .
JOURNAL OF ANTIBIOTICS, 1968, 21 (07) :454-&
[4]   STUDIES IN RELATION TO BIOSYNTHESIS .3. THE STRUCTURE OF ELEUTHERINOL [J].
BIRCH, AJ ;
DONOVAN, FW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1953, 6 (04) :373-378
[5]   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
[6]   SYNTHESIS OF SOME PRECURSORS OF 1,3,8-NAPHTHALENETRIOL AND RELATED COMPOUNDS [J].
CAMERON, DW ;
HILDYARD, EM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (02) :166-&
[7]   SYNTHESIS OF VENTILAGONE [J].
CAMERON, DW ;
CROSBY, IT ;
FEUTRILL, GI .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (12) :2025-2035
[8]   DIHYDROPYRAN DERIVATIVES FROM DIMERISATION OF CROTONALDEHYDE [J].
CAMERON, DW ;
SCHUTZ, PE .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (14) :1801-&
[9]   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
[10]   A NEW SYNTHESIS OF THE NAPHTHOPYRAN ANTIBIOTICS [J].
CAMERON, DW ;
CROSBY, IT ;
FEUTRILL, GI .
TETRAHEDRON LETTERS, 1992, 33 (20) :2855-2856