An unusual stereochemical outcome of radical cyclization: synthesis of (+)-biotin

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• 作者：Subhash P. Chavan ; Amar G. Chittiboyina ; Guduru Ramakrishna ; Rajkumar B. Tejwani ; T. Ravindranathan ; Subhash K. Kamat ; Beena Rai ; Latha Sivadasan ; Kamalam Balakrishnan ; S. Ramalingam and V.H. Deshpand
• 关键词：Biotin ; Radical cyclization ; Exocyclization
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：2005
• 年：2005
• 卷：61
• 期：39
• 页码：9273-9280
• 全文大小：213 K

文摘

An enantioselective synthesis of (+)-biotin 11 starting from naturally available cysteine is described. The key steps are the unusual stereochemical outcome of radical cyclization of compound 1010 to prepare 5,5-fused system 1111, and the introduction of C4-sidechain at C₆ in 1313 via a Grignard reaction.