Abstract
The indolic analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines were obtained by Fischer indole synthesis using the acetonylcyclopropanes derived from (+)-car-3-ene. The cyano- and N-cyanamido groups in the starting carbonyl compounds did not hinder indolization. The reduction of the nitrile group bound to the asymmetrical atom of the cyclopropane ring by LiAlH4 in ether can be accompanied by epimerization or racemization.
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Glushkov, V.A., Karmanov, V.I. & Shklyaev, Y.V. Synthesis of indole-containing analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines. Russian Chemical Bulletin 51, 1308–1318 (2002). https://doi.org/10.1023/A:1020969017314
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DOI: https://doi.org/10.1023/A:1020969017314