Synthesis of exogonic acid and related compounds

Tomihiro Nishiyama, Joanne F. Woodhall, Elvie N. Lawson, William Kitching*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

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-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 and involve sequential alkylation with epoxypropane and l,2-epoxy-4-(tetrahydropyranyloxy)butane of anions (or dianions) derived from methyl acetoacetate or acetone dimethylhydrazone.

Original languageEnglish
Pages (from-to)2183-2189
Number of pages7
JournalJournal of Organic Chemistry
Volume54
Issue number9
DOIs
Publication statusPublished - 28 Apr 1989
Externally publishedYes

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