Synthesis 2007(8): 1159-1164  
DOI: 10.1055/s-2007-965992
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Practical Formal Synthesis of d-(+)-Biotin from 4-Formylazetidin-2-one

Ajaykumar S. Kalea, Vedavati G. Puranikb, Abdul Rakeeb A. S. Deshmukh*a
a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
b Center for Materials Characterization, National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25902624; e-Mail: Abdulrakeeb.Deshmukh@emcure.co.in;
Further Information

Publication History

Received 19 July 2006
Publication Date:
28 March 2007 (online)

Abstract

A practical synthesis of (3S,6R)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione, an important intermediate in the synthesis of biotin, from 4-formyl-3-mesyloxyazetidin-2-one has been achieved. Acid-catalyzed azetidin-2-one ring opening followed by a one-pot conversion of diamine hydrochloride to a cyclic urea and hydroxymethylene to chloromethylene by triphosgene to obtain (4S,5R)-methyl-1,3-dibenzyl-5-chloromethyl-2-oxoimidazolidine-4-carboxylate is the key step in this synthesis.

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