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N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B
Ye, Zhao-Bao ; Chen, Jie ; Meng, Wei-Hua ; Huang, Pei-Qiang ; Huang PQ(黄培强)
2010-06
英文摘要O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.; NSF of China [20832005]; National Basic Research Program (973 Program) of China [2010CB833206]
语种英语
出版者PERGAMON-ELSEVIER SCIENCE LTD
内容类型期刊论文
源URL[http://dx.doi.org/doi:10.1016/j.tetasy.2010.04.063]  
专题化学化工-已发表论文
推荐引用方式
GB/T 7714
Ye, Zhao-Bao,Chen, Jie,Meng, Wei-Hua,et al. N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B[J],2010.
APA Ye, Zhao-Bao,Chen, Jie,Meng, Wei-Hua,Huang, Pei-Qiang,&黄培强.(2010).N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B..
MLA Ye, Zhao-Bao,et al."N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B".(2010).
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