A NEW APPROACH TO ALL-CIS TRIQUINANE SYNTHESIS AND A NEW ROUTE TO THE C16-HEXAQUINANE SYSTEM

Article abstract of DOI:10.1016/0040-4020(81)80015-4

A new synthesis of all-cis triquinanes is presented.The examples bear a cis substituent on the fifth position of the central ring, and are thus all-cis pentasubstituted cyclopentanes.The stereo-controlled addition of organometallics of 7-ketonorbornenes is considered, as is "reductive solvolysis" of such adducts to the corresponding hydrocarbons.The preparation of trans-3,4-dimethoxycyclopentyl chloride is given, as is that of the corresponding organolithium.The use of quinoxaline derivatives in aldol-type reactions is considered, with examples.A new approach to the C16-hexaquinane system is developed.The ring systems reported include: tricyclo<8.2.1.0^2,9>tridecane, tricyclo<6.3.0.0^3,7>undecane, tetracyclo<10.1.0.0^2,9.0^10,13>tridecane, pentacyclo<8.5.1.0.^2,6.0^7,16.0^11,15>hexadecane and hexacyclo<8.5.1.0^2,6.0^3,14.0^7,16.0^11,15>hexadecane.