De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.
De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.
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DOI：
10.1039/c4sc00593g
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发表时间：
2014-06
期刊：
影响因子：
8.4
通讯作者：
O'Doherty GA
中科院分区：
文献类型：
--
作者：
Bajaj SO;Sharif EU;Akhmedov NG;O'Doherty GA
Mezzettiside天然产品家族的任何和所有成员的首次合成已经实现。报道的合成方法是在亲核的硼/亲电的钯催化的区域选择性糖基化反应中反复使用泰勒催化剂。此外，从头开始的方法利用无原子保护基团和最少使用保护基团(用于合成10个天然产物的2个氯乙酸酯)。这些发散的合成发生在13到22个最长的线性步骤的范围内，并且只需要总共41个步骤来制备整个Mezzettiaside家族。
The first synthesis of any and all members of the mezzettiaside family of natural products has been achieved. The reported synthesis features the iterative use of the Taylor catalyst in a dual nucleophilic boron/electrophilic palladium catalyzed regioselective glycosylation. In addition, the de novo approach utilizes atomless protecting groups and the minimal use of protecting groups (2 chloroacetates for the synthesis of 10 natural products). These divergent syntheses occurred in a range of 13 to 22 longest linear steps and required only 41 total steps to prepare the entire family of mezzettiasides.