Absolute stereochemistry of exogonic acid

Elvie N. Lawson, Joanne F. Jamie, William Kitching*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspiro[4.4]nonane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin) is demonstrated to be predominantly the E,E and Z,Z diastereomers, with the 2S,5S,7R and 2S,5R,7R configurations, respectively. Minor amounts of the 2R,5S,7R E,Z and 2R,5R,7R Z,E isomers are also present. These conclusions are based on chiral gas chromatographic analyses of suitable derivatives and enantioselective syntheses employing (S)-1,2-epoxypropane and (2S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2-epoxybutane as alkylating agents for anions of acetone N,N-dimethylhydrazone.

Original languageEnglish
Pages (from-to)353-358
Number of pages6
JournalJournal of Organic Chemistry
Volume57
Issue number1
Publication statusPublished - 1992
Externally publishedYes

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