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

Ajaykumar S. Kale; Vedavati G. Puranik; Abdul Rakeeb A. S. Deshmukh

doi:10.1055/s-2007-965992

PAPER

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

Ajaykumar S. Kale^a, Vedavati G. Puranik^b, 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;

Abstract

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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.

Key words

β-lactams - cyclization - reduction - lactone - azetidin-2-one

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Referenzen

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