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Synlett 1991; 1991(2): 99-101
DOI: 10.1055/s-1991-20641
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(Trimethylsilyl)- and (Tributylstannyl) acetylenes as Nucleophiles Toward Acyliminium Cations: A Plausible Key Reaction for Dynemicin, an Enediyne Antitumor Antibiotic

Toshio Nishikawa* , Minoru Isobe, Toshio Goto
  • *Laboratory of Organic Chemistry, School of Agriculture, Nagoya University, Chikusa, Nagoya 464, Japan
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Publication Date:
07 March 2002 (online)

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Dynemicin A, a hexacyclic antitumor antibiotic with an enediyne medium-sized ring, has a peculiar propargyl amine moiety which was partially synthesized by coupling between (trimethylsilyl)- or (tributylstannyl)acetylenes and acyliminium cation species prepared from (E)-1-ethoxy-l-[ethoxycarbonyl (4-methoxyphenyl)amino]-3-phenyl-2-propene in the presence of a Lewis acid. The effects of reaction temperature, Lewis acid and the heteroatom (silicon or tin) on the coupling (1,2 versus 1,4) is also described.