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Synlett 1995; 1995(1): 41-42
DOI: 10.1055/s-1995-4855
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A Concise Synthesis of (+)-(S)-Dihydroperiphylline

Kazuaki Ishihara, Yoshichika Kuroki, Hisashi Yamamoto*
  • *School of Engineering, Nagoya University, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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The total synthesis of the spermidine alkaloid, (+)-(S)-dihydroperiphylline, is described. The key reactions in the present strategy are enantioselective aldol-type reaction of imines with ketene silyl acetals promoted by chiral BLA (Brønsted acid assisted chiral Lewis acid) and boron-templated cyclization of triamino esters.

(+)-(S)-dihydroperiphylline - spermidine alkaloid - Brønsted acid assisted chiral Lewis acid - aldol-type reaction of imines with ketene silyl acetals - boron-templated cyclization