Oxidative cyclization of tertiary pentenol derivatives forming 2,5,5-trisubstituted THF rings and the total synthesis of cyclocapitelline

TETRAHEDRON LETTERS

卷:56

Article

Phillips, Geoffrey A.¹  Palmer, Cory¹  Stevens, Andrew C.¹  Piotrowski, Mathew L.¹  Dekruyf, Daryl S. R.¹  Pagenkopf, Brian L.¹ 

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

关键词: Mukaiyama oxidative cyclization;    Co(nmP)(2);    Tetrahydrofuran;    Cyclocapitelline;    Cross metathesis;   

DOI  :  10.1016/j.tetlet.2015.09.064

来源: Elsevier

【 摘 要 】

The synthesis of 2,5,5-trisubstituted tetrahydrofuran rings was accomplished via the Mukaiyama aerobic oxidative cyclization of tertiary 5-pentenols employing the Co(nmp)(2) catalyst. A variety of THFs were formed in moderate to good yield and diastereoselectivity. The method developed herein was successfully applied to an enantioselective total synthesis of cyclocapitelline. (C) 2015 Elsevier Ltd. All rights reserved.

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