Dedicated to Professor Helmut Vorbrüggen on the occasion of his 90^th birthday

Abstract

The samarium diiodide promoted reductive cyclization of a series of γ-aryl ketones with acetoxy, alkoxy, and siloxy groups in ortho-, meta-, and para-positions was investigated. Only precursors with p-acetoxy, p-tert-butoxy, or p-siloxy substituents furnished decent yields of the desired 7-oxy-1,2,3,4,6,8a-hexahydronaphthalene derivatives. The products were formed without contamination with the regio­isomeric bicyclic products containing conjugated double bonds. Typical reactions exploiting the silyl enol ether moiety of the 7-(tert-butyl­dimethylsiloxy)-1,2,3,4,6,8a-hexahydronaphthalene derivative were performed, allowing stereoselective access to highly substituted hexahydro­-, octahydro-, or decahydronaphthalene derivatives.

中文翻译：

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7-甲氧基取代的六氢萘衍生物：二碘化Sa促进的合成和典型反应

专用于赫尔穆特Vorbrüggen教授在他的90之际^个生日

抽象

研究了二碘化sa促进了一系列γ-芳基酮在邻位，间位和对位的乙酰氧基，烷氧基和甲硅烷氧基的还原环化反应。只与前体p -乙酰氧基，p -叔丁氧基，或p得到所需7-氧- 1,2,3,4,6,8a-六氢化萘衍生物的收率体面甲硅烷氧基取代基。形成的产物没有被含有共轭双键的区域异构双环产物污染。利用7-（叔丁基的甲硅烷基烯醇醚部分的典型反应进行了-丁基二甲基甲硅烷氧基）-1,2,3,4,6,8a-六氢萘衍生物的制备，从而可以立体选择性地进入高度取代的六氢，八氢或十氢萘衍生物。