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Synlett 1996; 1996(9): 925-926
DOI: 10.1055/s-1996-5629
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Enantio- and Stereo-controlled Synthesis of the Nitraria Alkaloids, (+)-Nitramine, (+)-Isonitramine, and (-)-Sibirine

Takahiro Yamane, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81-22-217-6845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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All of three 2-azaspiro[5.5]undecan-8-ol alkaloids isolated from the Nitraria plants, (+)-nitramine, (+)-isonitramine, and (-)-sibirine, have been synthesized stereoselectively in natural forms starting from racemic 2-carbethoxy-2-cyclohexen-1-ol employing lipase-mediated kinetic resolution and radical cyclization as key steps.

Nitraria alkaloids - enantiocontrolled synthesis - chiral building block - lipase-mediated resolution - radical cyclization