Absolute stereochemistry of exogonic acid

Lawson E.N., Jamie J.F. and Kitching W. (1992) Absolute stereochemistry of exogonic acid. Journal of Organic Chemistry, 57 1: 353-358.

Author Lawson E.N.
Jamie J.F.
Kitching W.
Title Absolute stereochemistry of exogonic acid
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 1992-01-01
Sub-type Article (original research)
Volume 57
Issue 1
Start page 353
End page 358
Total pages 6
Subject 1605 Policy and Administration
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.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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Created: Sat, 09 Jul 2016, 16:02:08 EST by System User