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Stereocontrolled synthesis of (+)- and (−)-iridomyrmecin from citronellene enantiomers |
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| Authors: | A. V. Stepanov V. V. Veselovsky |
| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
| Abstract: | Natural (+)-iridomyrmecin and its unnatural enantiomer (−)-iridomyrmecin were synthesized by intramolecular [3+2] dipolar cycloaddition of silyl nitronates that had been generated from the nitro derivatives of (+)- and (−)-citronellenes, respectively. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1683–1687, September, 1997. |
| Keywords: | iridolactone (+)-iridomyrmecin (− )-isoiridomyrmecin (− )-iridomyrmecin (+)-β -citronellene (− )-β -citronellene silyl nitronate intramolecular [3+2] dipolar cycloaddition |
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