Tetrahedron

Conformational dependent regio-and stereo-selectivity in transformations of germacrenes: A theoretical and experimental approach

HR Fransen, GJM Dormans, HM Buck

Index: Fransen, Harrie R.; Dormans, Guido J. M.; Buck, Henk M. Tetrahedron, 1983 , vol. 39, # 18 p. 2981 - 2987

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Citation Number: 6

Abstract

Conformational calculations on 8-hydroxy-germacrene B 1 with the MNDO method led to a correct prediction of the most stable conformer. Reaction of 1 with diimide resulted in regio- selective reduction which leads to the formation of two racemic mixtures of 4, 5-dihydro-8- hydroxy-germacrene B (2+ 3). The ratio of 2 and 3 could be predicted by conformational analysis The regioselectivity of the reduction may be attributed to differences in sp2-sp3 ...