Domino Michael-aldol annulations for the stereocontrolled synthesis of bicyclo[3.3.1]nonane and bicyclo[3.2.1]octane derivatives

被引：16

作者：

Promontorio, Rossella ^{[1
,2
]}

Richard, Jean-Alexandre ^{[1
]}

Marson, Charles M. ^{[2
]}

机构：

[1] ASTAR, ICES, Organ Chem, 8 Biomed Grove,Neuros 07-01, Singapore 138665, Singapore

[2] UCL, Dept Chem, Christopher Ingold Labs, 20 Gordon St, London WC1H 0AJ, England

来源：

RSC ADVANCES | 2016年 / 6卷 / 115期

基金：

英国工程与自然科学研究理事会;

关键词：

POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; ALKYLATIVE DEAROMATIZATION-ANNULATION; HYPERFORIN; CHEMISTRY; (+/-)-CLUSIANONE; CONSTRUCTION; BRIDGEHEAD;

D O I：

10.1039/c6ra23523a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Domino Michael-aldol annulation of cycloalkane-1,3-diones with enals affords a general route to 6-hydroxybicyclo[ 3.3.1] nonane-2,9-diones and 2-hydroxybicyclo[3.2.1] octane-6,8-diones, notably in one-pot procedures under convenient conditions. The annulation is shown to be compatible with one or more substituents at six positions of the bicyclo[3.3.1] nonane-2,9-dione scaffold. In some cases, the relative configuration of the product can be controlled by the appropriate choice of solvent, base and temperature for the annulation. In contrast to the chair-chair conformations usually adopted, the bicyclo compounds derived from 2,4,4-trimethylcyclohexane-1,3-dione possessed boat-chair conformations. Oxidation of the annulation products gave the corresponding bicyclo triketones.

引用

页码：114412 / 114424

页数：13

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