Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs.
Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs.
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DOI：
10.1039/c2sc00866a
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发表时间：
2012-01-01
期刊：
影响因子：
8.4
通讯作者：
Montgomery J
中科院分区：
文献类型：
--
作者：
Shareef AR;Sherman DH;Montgomery J
发展了醛和末端炔还原大环化反应的区域化学逆转策略。使用一种先进的合成中间体，针对大环内酯类化合物，选择性内环化提供天然的十二元环系列，而配体改变使选择性外环化提供非天然的十一元环系列。十二元环加合物转化为10-脱氧甲基内酯，完成了这一天然产物的高效全合成。
A strategy for regiochemical reversal of reductive macrocyclizations of aldehydes and terminal alkynes has been developed. Using an advanced synthetic intermediate directed towards the methymycin/neomethymycin class of macrolides, selective endocyclization provides the natural twelve-membered ring series, whereas ligand alteration enables selective exocyclization to provide access to the unnatural eleven-membered ring series. The twelve-membered ring adduct was converted to 10-deoxymethynolide, completing an efficient total synthesis of this natural product.