Syntheses of isochromane analogues of the michellamines and korupensamines

被引：36

作者：

de Koning, CB ^{[1
]}

Michael, JP ^{[1
]}

van Otterlo, WAL ^{[1
]}

机构：

[1] Univ Witwatersrand, Dept Chem, Ctr Mol Design, ZA-2050 Johannesburg, South Africa

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 05期

关键词：

D O I：

10.1039/a908367g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of the oxygen analogues 6, 7 and 8 of the michellamines 1 and korupensamines 2 are described. Racemic 5-iodo-6,8-dimethoxy-trans-1,3-dimethylisochromane 10 was synthesised in eleven steps from 2,4-dimethoxybenzaldehyde in an overall yield of 51%. The isopropoxy analogue 11 was synthesised in a similar manner. Isochromane 10 was coupled using Suzuki methodology with 4-isopropoxy-5-methoxy-7-methylnaphthalene-1-boronic acid 9 to produce 7 in 96% yield. This was converted in good yield into the desired product 6 by oxidative dimerisation followed by reduction of the cross-conjugated ene-dione intermediate 45.

引用

页码：799 / 811

页数：13

共 65 条

[41] NOVEL ALKALOIDS FROM THE TROPICAL PLANT ANCISTROCLADUS-ABBREVIATUS INHIBIT CELL KILLING BY HIV-1 AND HIV-2 [J].

MANFREDI, KP ;

BLUNT, JW ;

CARDELLINA, JH ;

MCMAHON, JB ;

PANNELL, LL ;

CRAGG, GM ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (12) :3402-3405

[42] MICHELLAMINE-B, A NOVEL PLANT ALKALOID, INHIBITS HUMAN IMMUNODEFICIENCY VIRUS-INDUCED CELL-KILLING BY AT LEAST 2 DISTINCT MECHANISMS [J].

MCMAHON, JB ;

CURRENS, MJ ;

GULAKOWSKI, RJ ;

BUCKHEIT, RW ;

LACKMANSMITH, C ;

HALLOCK, YF ;

BOYD, MR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (02) :484-488

[43] 3-(ALKOXYPHENOXY)-1,2-PROPANEDIOLS [J].

MELTZER, RI ;

DOCZI, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) :4986-4988

[44] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[45] Novel palladium(0)-catalyzed coupling reaction of dialkoxyborane with aryl halides: Convenient synthetic route to arylboronates [J].

Murata, M ;

Watanabe, S ;

Masuda, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6458-6459

[46]

Pschorr R, 1912, LIEBIGS ANN CHEM, V391, P23

[47]

Rao AVR, 1996, HETEROCYCLES, V43, P1

[48] DEHYDROXYLATION OF PHENOLS BY CLEAVAGE OF THEIR DIETHYL PHOSPHATE ESTERS WITH ALKALI-METALS IN LIQUID-AMMONIA [J].

ROSSI, RA ;

BUNNETT, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (13) :2314-2318

[49]

ROZWADOWSKA MD, 1994, HETEROCYCLES, V39, P903

[50]

Schilling B, 1998, EUR J ORG CHEM, V1998, P701

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