119681-01-5Relevant academic research and scientific papers
Synthesis of Exogonic Acid and Related Compounds
Nishiyama, Tomihiro,Woodhall, Joanne F.,Lawson, Elvie N.,Kitching, William
, p. 2183 - 2189 (2007/10/02)
Hydroxymercuration, cyclization, and reduction of appropriate hydroxy ketones or enones carrying a suitably located α,β-unsaturated ester function is an efficient route to exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspirononane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin), and related and spiroketal systems.Procedures incorporating stereocontrol at C-2 and C-7 of exogonic acid are also reported and involve sequential alkylation with epoxypropane and 1,2-epoxy-4-(tetrahydropyranyloxy)butane of anions (or dianions) derived from methyl acetoacetate or acetone dimethylhydrazone.
