Highly Exo-Selective Epoxidation and Hydroxylation of Triquinacene and Its Derivatives: all-exo-Hexahydroxytriquinane.
Epoxidation of triquinacene 3 with dimethyldioxirane proceeded with a high degree of exo-face selectivity to give a quantitative yield of a 1:1.5 mixture of all-exo-4a and endo,exo,exo-triepoxytriquinane 4b. Subsequent lithium aluminum hydride reduction of the all-exo-triepoxide 4a gave all-exo-2,5,8-5a and all-exo-2,5,9-trihydroxytriquinane 5b, respectively. The straightforward 3-fold dihydroxylation of triquinacene 3 led exclusively to the all-exo-hexahydroxytriquinane 8 in one step. X-ray crystal structure analyses confirmed the configuration of the triepoxide 4b and the hexaacetate 9 of the hexol 8.
Haag
Rainer
R
Institut für Organische Chemie and Institut für Anorganische Chemie,Georg-August-Universität Göttingen, Tammannstrasse 2-4, D-37077 Göttingen, Germany.
Zuber
Richard
R
Donon
Sylvie
S
Lee
Chi-Hung
CH
Noltemeyer
Matthias
M
Johnsen
Keyji
K
de Meijere
Armin
A