通过构象控制的非对映选择性内酰胺环扩展不对称合成(-)-6-去甲氟尿苷 A₁。
Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A₁ via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions.
机构信息
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea.
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea.
出版信息
Molecules. 2018 Sep 14;23(9):2351. doi: 10.3390/molecules23092351.
The versatile synthesis of (-)-6-desmethyl-fluvirucinine A₁ was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors.
（-）-6-去甲氟维菌素 A₁的综合合成是通过从已知的乙烯基哌啶出发，经过十三步反应，以 24%的总收率实现的。关键部分涉及通过构象诱导的非对映选择性控制和酰胺前体的迭代氮杂-Claisen 重排，来精心构建远端的立体中心和大环内酯骨架。
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