Synthesis of chlorobiumquinone

H Rapoport, CD Snyder…

Index: Snyder,C.D. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 25 p. 3951 - 3960

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Abstract

The synthesis of chlorobiumquinone, a2Z-trans-l'-oxomenaquinone-7, is reported. A key intermediate in this synthesis is the naphthalenic fragment, 2-lithio-3-methyl-l, 4- dimethoxynaphthalene, which when condensed with an a, p-unsaturated aldehyde side- chain component yields the dimethyl ether of 1'-oxymenaquinol. This allylic alcohol can either be oxidatively demethylated with acidic argentic oxide (Ago), leading to a 1'- ...