次溴酸异莰烷酯的光分解反应及其在Noji菊醇合成中的应用

The Photo-Induced Decomposition of lsc-Camphanyl Hypobromites and its Application in the Synthesis of Nojigiku Alcohol

Barton反应可选择性地在未活化碳原子上导入活性基团,咽此被广泛应用于有机合成，异莰烷醇的Barton反应似亦可将异莰烷的骨架碳活化，1968年Lhomme等报道了异莰烷醇的四醋酸铅氧化反应，endo-异莰烷醇（1）和exo－异莰烷醇（2）反应分别得到环醚3和4，但环醚得率低，主要产物是醋酸异莰烷酯，本文研究了异莰烷醇两种异构体在Br2-HgO 光照条件下的Barton反应，得到3和4，产率较高，由环醚3开环经五步转化选择性地合成了Noji菊醇（Nojigiku Alcohol5)；环醚4可作为β-檀香醇（6）合成中的潜在中间体。

The photo-induced decomposition of endo-and exo-isocamphanyl hypobromites in n- pentane was studied, which resulted in the formation of isomeric cyclic ethers 3 and 4 respectively. Nojigiku alcohol (5), a monoterpene alcohol isolated from Chrysanthemum japonese, was synthesized from the cyclic ether 3 via a five-sequence.