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Elsevier, Tetrahedron, 34(67), p. 6281-6288

DOI: 10.1016/j.tet.2011.06.023

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A new approach to the C(28) fatty acid chain of the marine natural products schulzeines B and C: a concise diastereoselective total synthesis of (-)-schulzeine B

Journal article published in 2011 by Chao Yang, 王爱娥, 黄培强, Yu-Hui Bao, Pan Liang, Jian-Liang Ye, Ai-E. Wang, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

An enantioselective approach to the C(28) fatty acid chain of the marine natural products schulzeines B and C was established based on the L-tartaric acid derived C(4) chiron 11 via successive 1,4-bis-chain elongation reactions and catalytic asymmetric hydrogenation. The chiral tricyclic core 8 was constructed via a diastereoselective Pictet-Spengler cyclization reaction (dr = 89:11) of the L-glutamic acid derived precursor 13. On this basis, a concise total synthesis of (-)-schulzeine B (5) was disclosed. (C) 2011 Elsevier Ltd. All rights reserved. ; NSF of China[20832005, 21072160]; NFFTBS[J1030415]; National Basic Research Program (973 Program) of China[2010CB833200]