Stereoselective synthesis of microcarpalide.
The first total synthesis of the naturally occurring nonenolide, microcarpalide, is described. The key step in the synthesis was the ring-closing metathesis of a dienic ester prepared in turn by coupling an acid and an alcohol stereoselectively synthesized from (S,S)-tartaric acid and (R)-glycidol, respectively. [structure: see text]
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005658:Fungi / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000473:Alkanes; D006573:Heterocyclic Compounds, 1-Ring; C442266:microcarpalide