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Synlett 2014; 25(20): 2879-2882
DOI: 10.1055/s-0034-1379365
letter
© Georg Thieme Verlag Stuttgart · New York

A Facile and Convenient Synthesis of (±)-Biotin via MgCl2/Et3N-Mediated C–C Coupling and Mitsunobu Reaction

Subhash P. Chavan*
Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India   Fax: +91(20)25902629   eMail: sp.chavan@ncl.res.in
,
Prakash N. Chavan
Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India   Fax: +91(20)25902629   eMail: sp.chavan@ncl.res.in
,
Pradeep B. Lasonkar
Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India   Fax: +91(20)25902629   eMail: sp.chavan@ncl.res.in
,
Lalit B. Khairnar
Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India   Fax: +91(20)25902629   eMail: sp.chavan@ncl.res.in
,
Appasaheb L. Kadam
Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India   Fax: +91(20)25902629   eMail: sp.chavan@ncl.res.in
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Publikationsverlauf

Received: 08. Juli 2014

Accepted after revision: 29. September 2014

Publikationsdatum:
05. November 2014 (online)

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Abstract

A synthesis of (±)-biotin is described starting from simple starting materials viz. cyclohexanone and amino malonic acid ester. The key steps involved are MgCl2/Et3N coupling of amino malonic acid ester derivative and acid chloride, Mitsunobu reaction, ozonolysis, Staudinger reduction, novel urea formation, and subsequent dibenzylation. This approach is economical and involves high-yielding steps and simple reaction conditions.

Key words

biotin - ozonolysis - Appel reaction - Mitsunobu reaction - Staudinger reduction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
  • Supporting Information
 

  • References and Notes

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