Synthetic approach toward alpha-aminomethyl-gamma-butyrolactones from beta-lactam synthons elaborated by SmI2-mediated reductive coupling reactions

Masaki Takahashi; Takahiro Sudo; Yusuke Murata; Tetsuya Sengoku; Hidemi Yoda

Synthetic approach toward alpha-aminomethyl-gamma-butyrolactones from beta-lactam synthons elaborated by SmI2-mediated reductive coupling reactions

Nat Prod Commun. 2013 Jul;8(7):889-96.

Authors

Masaki Takahashi¹, Takahiro Sudo, Yusuke Murata, Tetsuya Sengoku, Hidemi Yoda

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, Shizuoka 432-8561, Japan.

PMID: 23980417

Abstract

A simple and straightforward synthetic approach was developed to access a biologically important class of alpha-aminomethyl-gamma-butyrolactones via a beta-lactam synthon strategy involving successive ring-opening and lactonization processes from alpha-hydroxyethyl-substituted beta-lactams that were elaborated by SmI2-mediated reductive coupling reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives
Iodides / pharmacology
Lactones / chemical synthesis*
Lactones / chemistry
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Samarium / pharmacology
beta-Lactams / chemistry*

Substances

Iodides
Lactones
beta-Lactams
Samarium
samarium diiodide
4-Butyrolactone