Acid-induced atypical spontaneous conversion of 5-amino-2,6-dioxooctahydro-1H-pyrrolo[2,1-d][1,5]oxazocine into 4-(hydroxymethyl)-2,5-dioxooctahydro-1H-pyrrolo[1,2-d][1,4]diazepine

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• 作者：Zhaojun Sheng ; Chang-Zhi Dong ; Zhiyun Du ; Yiming Shi…
• 关键词：Yamaguchi lactonization ; Proline ; like ; Lactone ; Lactam ; HMBC ; Non ; peptide mimetics
• 刊名：Research on Chemical Intermediates
• 出版年：2015
• 出版时间：October 2015
• 年：2015
• 卷：41
• 期：10
• 页码：7179-7187
• 全文大小：628 KB
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• 作者单位：Zhaojun Sheng (1) (2)
  Chang-Zhi Dong (1) (2)
  Zhiyun Du (1)
  Yiming Shi (2) (3)
  Fr茅d茅rique Pallois (2)
  Yang Lu (3)
  Kun Zhang (1)
  
  1. Institute of Natural Medicine and Green Chemistry, Guangdong University of Technology, Guangzhou, 510006, People鈥檚 Republic of China
  2. ITODYS, UMR 7086 CNRS, Universit茅 Paris Diderot, Sorbonne Paris Cit茅, 15 rue J-A de Ba茂f, 75205, Paris Cedex 13, France
  3. Department of Pharmacy, Basic Medical College, Shanghai Jiaotong University, Shanghai, 200025, People鈥檚 Republic of China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

(5S,8S,10aR)-tert-butyl 5-(tert-butoxycarbonylamino)-2,6-dioxooctahydro-1H-pyrrolo[2,1-d][1,5]oxazocine-8-carboxylate 5, containing an original proline-like moiety, was prepared through Yamaguchi lactonization. However, it was observed that this 8 + 5 bicyclic lactone was spontaneously rearranged to the corresponding 7 + 5 bicyclic lactam under acid conditions, used to remove the Boc/tBu protecting groups. Both core structures were confirmed by one-dimensional and two-dimensional NMR, as well as HRMS. The new proline-like moieties are unknown up to now, and the 7 + 5 bicyclic lactam, much more stable than its precursor, may represent a valuable template to develop constrained non-peptide mimetics. Keywords Yamaguchi lactonization Proline-like Lactone Lactam HMBC Non-peptide mimetics