Stereoselective Synthesis of Functionalized cis-Hydrindanes from 2-exo Carbomethoxytricyclo188.8.131.52(2,6)deca-3,8-diene-5-ones
AIR FORCE RESEARCH LAB EDWARDS AFB CA PROPULSION DIRECTORATE WEST
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Compounds having bicyclo4.3.Ononane cis-hydrindane carbon skeleton or embedded as a core unit in their structure are widely distributed in nature. Several synthetic methodologies for cis-hydrindane have been developed while aiming at the synthesis of specific target molecule. The bicyclo4.3.Ononane skeleton is enclosed within tricyclo5.2.L.2,6decane carbon framework. The extraction of a cis-hydrindane carbon skeleton from tricyclo5.2.1 .O2,6decane 2 carbon framework is very attractive since stereofacial bias inherent in 2 should allow elaboration of the cis-hydrindane 1 with high degree of stereoselectivity. The detailed account for the stereoselective synthesis of functionalized cis-hydrindanes from 2-exo- carbomethoxytricyclo5.2.1.O2,6deca-3,8-diene-5-one and its methyl derivatives shall be presented.
- Organic Chemistry