Concise Synthesis of the Bryostatin A-Ring via Consecutive C-C Bond Forming Transfer Hydrogenations
Concise Synthesis of the Bryostatin A-Ring via Consecutive C-C Bond Forming Transfer Hydrogenations
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DOI：
10.1021/ol901096d
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发表时间：
2009-07-16
期刊：
影响因子：
5.2
通讯作者：
Krische, Michael J.
中科院分区：
文献类型：
--
作者：
Lu, Yu;Krische, Michael J.
在C-C键形成的转移氢化条件下，1，3-丙二醇1进行双不对称羰基烯丙基化反应，得到C-2-对称二醇2。2的双重臭氧分解，然后TBS保护，得到醛3，其通过转移氢化进行催化剂指导的羰基反向异戊二烯化，得到新戊醇4，并最终得到苔藓抑素A-环7。通过使用两个连续的C-C键形成转移氢化，Evans苔藓抑素A-环7的制备不到以前报道的操作的一半。
Under the conditions of C-C bond forming transfer hydrogenation, 1,3-propanediol 1 engages in double asymmetric carbonyl allylation to furnish the C-2-symmetric diol 2. Double ozonolysis of 2 followed by TBS protection delivers aldehyde 3, which is subject to catalyst directed carbonyl reverse prenylation via transfer hydrogenation to deliver neopentyl alcohol 4 and, ultimately, the bryostatin A-ring 7. Through use of two consecutive C-C bond forming transfer hydrogenations, the Evans' bryostatin A-ring 7 is prepared in less than half the manipulations previously reported.