Tetrahedron p. 4479 - 4494 (1981)
Update date:2022-08-03
Topics:
Eaton, Philip E.
Sidhu, Ravinder S.
Langford, Gordon E.
Cullison, David A.
Pietruszewski, Cornel L.
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<8.2.1.02,9>tridecane, tricyclo<6.3.0.03,7>undecane, tetracyclo<10.1.0.02,9.010,13>tridecane, pentacyclo<8.5.1.0.2,6.07,16.011,15>hexadecane and hexacyclo<8.5.1.02,6.03,14.07,16.011,15>hexadecane.
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(1982)