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Synlett 1991; 1991(10): 719-720
DOI: 10.1055/s-1991-34776
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Preparation of a 3-Hydroxymethyl-2,4-pentadienyltin Reagent and Its Use in Alkaloid Synthesis; An Efficient Route to (±)-Nitraraine

Ryohei Yamaguchi* , Takashi Hamasaki, Tohru Sasaki, Sinpei Kozima, Hidemasa Takaya
  • *Department of Chemistry, College of Liberal Arts and Sciences, Kyoto University, Yoshida, Kyoto 606, Japan
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Publication Date:
13 March 2002 (online)

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A new functionalized organotin reagent, 3-hydroxymethyl-2,4-pentadienyltrimethylstannane (6), has been prepared via the 3-oxidomethylpentadienyl dianion. The three-component coupling reaction of 6 with 3,4-dihydro-ß-carboline (4) and acryloyl chloride provides an efficient method for the synthesis of the pentacyclic allo-yohimbane system 9 bearing a functionalized one-carbon unit at the C16 position, from which (±)-nitraraine (3) is readily synthesized.

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