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

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