Chemoenzymatic synthesis of (3S,4S)- and (3R,4R)-3-methoxy-4-methylaminopyrrolidine

doi:10.1016/j.tetlet.2004.08.167

Tetrahedron Letters

Volume 45, Issue 43, 18 October 2004, Pages 8057-8059

https://doi.org/10.1016/j.tetlet.2004.08.167 Get rights and content

Abstract

Facile chemoenzymatic enantioselective synthesis of (3S,4S)-3-methoxy-4-methylaminopyrrolidine, a key intermediate for a new quinolone antitumor compound AG-7352 has been described. This methodology illustrates the preparation of 3-azido-1-benzyloxycarbonyl-4-hydroxypyrrolidine starting from diallylamine via 1-benzyloxycarbonyl-3-pyrroline obtained by ring-closing metathesis (RCM) employing Grubbs’ catalyst. Enzymatic transesterification employing PS-C lipase gave (3S,4S)-3-azido-1-benzyloxycarbonyl-4-hydroxypyrrolidine in >99% ee, which upon methylation of the hydroxyl group followed by sequential reactions gave the desired intermediates, (3S,4S)-1-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-4-methoxypyrrolidine.

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Acknowledgements

One of the authors (A.K.) is thankful to the Department of Science and Technology, New Delhi and the Japan Society for the Promotion of Science for the award of JSPS Invitation fellowship to work in Japan. Three other authors (A.A.S., M.S., and M.S.M.) are also thankful to CSIR, New Delhi for the award of research fellowship.

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Chemoenzymatic synthesis of (3S,4S)- and (3R,4R)-3-methoxy-4-methylaminopyrrolidine

Abstract

Graphical abstract

Section snippets

Acknowledgements

Antimicrob. Agents Chemother.

Antimicrob. Agents Chemother.

J. Med. Chem.

Biochemistry

J. Med. Chem.

Chem. Soc. Rev.

Tetrahedron: Asymmetry

Nat. Prod. Rep.

Tetrahedron: Asymmetry

Tetrahedron: Asymmetry

Chem. Pharm. Bull.

Chem. Pharm. Bull.