(Trimethylsilyl)- and (Tributylstannyl) acetylenes as Nucleophiles Toward Acyliminium Cations: A Plausible Key Reaction for Dynemicin, an Enediyne Antitumor Antibiotic
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (02) , 99-101
- https://doi.org/10.1055/s-1991-20641
Abstract
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.Keywords
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