A new approach to the C28 fatty acid chain of the marine natural products schulzeines B and C: a concise diastereoselective total synthesis of(−)-schulzeine B |
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| Authors: | Chao YangYu-Hui Bao Pan LiangJian-Liang Ye Ai-E WangPei-Qiang Huang |
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| Institution: | Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China |
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| Abstract: | An enantioselective approach to the C28 fatty acid chain of the marine natural products schulzeines B and C was established based on the l-tartaric acid derived C4 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. |
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| Keywords: | Marine natural products Total synthesis Tartaric acid Glycosidase inhibitors benzo[a]quinolizidine |
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