Syntheses and chiroptical properties of C2-bissecocubane (tricyclo [4.2. 0.03, 6] octane) derivatives

M Nakazaki, K Naemura, Y Sugano…

Index: Nakazaki, Masao; Naemura, Koichiro; Sugano, Yasuyoshi; Kataoka, Yasuto Journal of Organic Chemistry, 1980 , vol. 45, # 16 p. 3232 - 3236

Full Text: HTML

Citation Number: 10

Abstract

(+)-2, 6~~ Dioxotricyclo [3.3. 2.03~ 7] decane-l, 5-dicarboxylic acid (18) was converted into the dibromo diketone (-)-lo, whose double Favorskii ring contraction afforded (-)-C2- bissecocubane-3, 6-dicarboxylic acid (12). Circular dichroism (CD) spectral comparison of the (-)-diketone 20, derived from (-)-lo, with (+)-(lS, 3R, GR, 8S)-hornoadamantane-2, 7- dione (31) assigned the (lS, 3R, 5S, 7R) configuration to (4-20, indicating the presence of ...