Tetrahedron p. 5995 - 6002 (1989)
Update date:2022-08-04
Topics:
Herczegh, Pal
Zsely, Martina
Szilagyi, Laszlo
Dinya, Zoltan
Bognar, Rezsoe
A mixture of tetrachiral deca-1,7E,9-triene 5 and its 7Z isomer 6 was prepared from D-glucose by the use of two Wittig olefination reactions.When 5 or 6 were subjected to intramolecular Diels-Alder reaction under thermal conditions the same, cis-fused octahydronaphtalene enantiomer 9 was formed exclusively.This phenomenom can be explained by Z-->E isomerization of 6 to 5.Similarly, when a mixture of trienones 7 and 8 was heated at 160 deg C the formation of a single product 10 was observed.Stereochemical outcome of the reactions can be rationalized by inspection of the possible conformers leading to transition states.
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