Synthesis of exogonic acid and related compounds

T Nishiyama, JF Woodhall, EN Lawson…

Index: Nishiyama, Tomihiro; Woodhall, Joanne F.; Lawson, Elvie N.; Kitching, William Journal of Organic Chemistry, 1989 , vol. 54, # 9 p. 2183 - 2189

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Citation Number: 17

Abstract

Hydroxymercuration, cyclization, and reduction of appropriate hydroxy ketones or enones carrying a suitably located a, &unsaturated ester function is an efficient route to exogonic acid (2-(carboxymethyl)-7-methyl-1, 6-dioxaspiro [4.4] nonane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin), and related [4.5] and [5.5] spiroketal systems. Procedures incorporating stereocontrol at C-2 and C-7 of exogonic acid are also reported ...