Facile and convenient synthesis of (+/-)-Biotin via MgCl2/Et3N-mediated C-C coupling and mitsunobu reaction

TitleFacile and convenient synthesis of (+/-)-Biotin via MgCl2/Et3N-mediated C-C coupling and mitsunobu reaction
Publication TypeJournal Article
Year of Publication2014
AuthorsChavan, SP, Chavan, PN, Lasonkar, PB, Khairnar, LB, Kadam, AL
JournalSynlett
Volume25
Issue20
Pagination2879-2882
Date PublishedDEC
Type of ArticleArticle
ISSN0936-5214
KeywordsAppel reaction, biotin, Mitsunobu reaction, Ozonolysis, Staudinger reduction
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.

DOI10.1055/s-0034-1379365
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.323
Divison category: 
Organic Chemistry