ELECTROPHILIC OLEFIN HETEROCYCLIZATION IN ORGANIC SYNTHESIS. : STEREOSELECTIVE INTRAMOLECULAR AMIDOMERCURATION OF γ-HYDROXY-δ, ε-UNSATURATED URETHANES

Hiroki TAKAHATA; Mayumi TAJIMA; Yasunori BANBA; Takefumi MOMOSE

doi:10.1248/cpb.37.2550

Hiroki TAKAHATA, Mayumi TAJIMA, Yasunori BANBA, Takefumi MOMOSE

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Keywords: electrophilic olefin heterocyclization, amidomercuration, γ-hydroxy-δ, ε-unsaturated urethane, pyrrolidine, 1, 2-relative asymmetric induction, detoxinine, slaframine, 3-hydroxyglutamic acid

JOURNAL FREE ACCESS

1989 Volume 37 Issue 9 Pages 2550-2552

DOI https://doi.org/10.1248/cpb.37.2550

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Abstract

Mercuric acetate driven cyclization of γ-hydroxy-δ, ε-unsaturated urethanes 1a, b proceeded regio- and stereoselectively to afford cis-2-acetoxymercurymethyl-3-hydroxypyrrolidines 2a, b, respectively. These were transformed into the key intermediates for several biologically active compounds.

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