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

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

doi:10.1248/cpb.40.2308

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

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

JOURNAL FREE ACCESS

1992 Volume 40 Issue 9 Pages 2308-2312

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

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Abstract

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.

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