Cleavage of ring A and formation of an unusual nor-triterpene skeleton via the Baeyer-Villiger reaction

TETRAHEDRON LETTERS

卷:53

Article

Tag, Ozgur²  Cagir, Ali³  Khan, Ikhlas A.⁴  Bedir, Erdal¹ 

[1] Ege Univ, Fac Sci, Dept Bioengn, TR-35100 Bornova, Turkey

[2] Ege Univ, Fac Sci, Dept Chem, TR-35100 Bornova, Turkey

[3] Izmir Inst Technol, Fac Sci, Dept Chem, TR-35430 Urla Izmir, Turkey

[4] Univ Mississippi, Sch Pharm, Dept Pharmacognosy, University, MS 38677 USA

关键词: Cycloastragenol;    Semi-synthesis;    Baeyer-Villiger;    3,5-Seco-4-nor-triterpenes;   

DOI  :  10.1016/j.tetlet.2012.08.068

来源: Elsevier

【 摘 要 】

With the aim to generate a compound library for our biological screening studies, cycloastragenol was subjected to chemical transformation studies. The Baeyer-Villiger oxidation experiments provided an interesting 3,5-seco-4-nor-triterpene skeleton via ring opening followed by an unusual rearrangement. A new methodology is described for transforming triterpenoids into 3,5-seco-4-nor derivatives. (C) 2012 Elsevier Ltd. All rights reserved,

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