Carbamoylmethl Radical Cyclization : Formal Synthesis of (-)-Trachelanthamidine

Tatsunori SATO; Katsuhiro TSUJIMOTO; Ken-ichiro MATSUBAYASHI; Kiroyuki ISHIBASHI; Masazumi IKEDA

doi:10.1248/cpb.40.2308

著者情報

キーワード: carbamoylmethyl radical, (S)-prolinol, α-chlorosulfide, tributyltin hydride, radical cyclization, 5-exo-tring cyclization, diastereoselectivity, pyrrolizidin-3-one, (-)-trachelanthamidine, Barbier-Wieland degradation

ジャーナルフリー

1992 年 40 巻 9 号 p. 2308-2312

DOI https://doi.org/10.1248/cpb.40.2308

詳細

抄録

Tributyltin hydride-mediated radical cyclization of the (2S)-N-(α-chloroacetyl)-2-ethenylpyrrolidines 13a, b and 15 and the bis(phenylthio)acetyl congener-14 derived from (S)-prolinol gave (1R, 7aS)-hexahyrdo1-methyl-3H-pyrrolizin-3-one (17) and its derivatives 16a, b in highly regio- and diastereo-selective manner. This radical cyclization was successfully applied to the formal total synthesis of (-)-trachelanthamidine.

責任著者(Corresponding author)

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