Ring Rearrangement Metathesis of 2-Allybicyclo[2.2.2]octenes A Short Entry to cis-Hydroindenols from 2-Methoxyphenols

• Main Authors: Kuo-Wei Tsao, 曹國緯
• Other Authors: Chun-Chen Liao
• Format: Others
• Language: zh-TW
• Published: 2008
• Online Access: http://ndltd.ncl.edu.tw/handle/59657954877965762076

碩士 === 國立清華大學 === 化學系 === 96 === The cis-hydrindanol skeleton can be found in the structures of many natural products, such as Botrydial、Sesquiterpene and Presilphiperfolan-8b-ol. Thus, in this thesis we report a short entry to functionalized cis-Hydroindenols from Diels-Alder reactions with masked o-benzoquinone (MOB) and the Ring- Rearrangement Metathesis (RRM).The bicyclo[2.2.2]octenone derivatives prepared for the RRM reaction were obtained from the Diels-Alder reaction of MOBs with various dienophiles, and followed by the addition of allylmagnesium bromide-CeCl3 complex. We have then successfully constructed cis-hydrindanol skeleton by this strategy and explored the scope and limitation of the target synthetic method.