Toward the total synthesis of hygrocin B and divergolide C: construction of the naphthoquinone-azepinone core.

Toward the total synthesis of hygrocin B and divergolide C: construction of the naphthoquinone-azepinone core.
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潮霉素 B 和地藜高利特 C 的全合成:萘醌-氮杂酮核心的构建。

DOI:
10.1021/ol5003847
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发表时间:
2014
期刊:
影响因子:
5.2
通讯作者:
Nawrat CC
Nawrat CC
中科院分区:
化学1区
文献类型:
--
作者:
Nawrat CC

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提出了一种高度区域选择性的Diels-Alder方法来研究生物活性天然产物氢素B和发散内酯C。该路线使用了一种不寻常的苯醌-氮平酮二酚,由8-甲氧基-1-萘酸乙酯经8步制备而成,其路线包括,作为关键步骤,桦木烷基化和四酮肟的贝克曼重排,两者都在多重图尺度上得到了证明。萘醌-氮平酮核心被适当地功能化,以添加天然产物中的ansa链。
A highly regioselective Diels–Alder approach toward the bioactive natural products hygrocin B and divergolide C is presented. The route uses an unusual benzoquinone–azepinone dienophile prepared in 8 steps from ethyl 8-methoxy-1-naphthoate, by a route which includes, as key steps, a Birch alkylation and a Beckmann rearrangement of a tetralone oxime, both of which are demonstrated on multigram scale. The naphthoquinone–azepinone core is suitably functionalized for addition of the ansa-chain, found in the natural products.
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