Synthesis of an isochroman analogue of the michellamines

被引:37
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 Wits, South Africa
关键词
biaryls; naphthalenes; isochromans; Suzuki coupling;
D O I
10.1016/S0040-4039(99)00318-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of racemic 5-iodo-6, 8-dimethoxy-1,3-trans-dimethylisochroman (16) in eleven steps from 2,4-dimethoxybenzaldehyde is outlined. Compound (16) was coupled by means of Suzuki methodology with 4-isopropoxy-5-methoxy-7-methylnaphthaleneboronic acid (19) to yield (20). This was converted into (6), a racemic isochroman analogue of the michellamines. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3037 / 3040
页数:4
相关论文
共 27 条
[21]   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
[22]   Catalytic cross-coupling reactions in biaryl synthesis [J].
Stanforth, SP .
TETRAHEDRON, 1998, 54 (3-4) :263-303
[24]   ORGANOBORATES IN NEW SYNTHETIC REACTIONS [J].
SUZUKI, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (06) :178-184
[25]  
SY WW, 1993, TETRAHEDRON LETT, V34, P6223
[26]   The synthesis and biological activity of two analogs of the anti-HIV alkaloid michellamine B [J].
Upender, V ;
Pollart, DJ ;
Liu, J ;
Hobbs, PD ;
Olsen, C ;
Chao, WR ;
Bowden, B ;
Crase, JL ;
Thomas, DW ;
Pandey, A ;
Lawson, JA ;
Dawson, MI .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) :1371-1384
[27]   Structural analogues of the michellamine anti-HIV agents. Importance of the tetrahydroisoquinoline rings for biological activity [J].
Zhang, HP ;
Zembower, DE ;
Chen, ZD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (20) :2687-2690