Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids.
Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids.
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DOI：
10.1002/chem.201701008
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发表时间：
2017-04
期刊：
影响因子：
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通讯作者：
J. Krieger;Toni Smeilus;Oliver Schackow;A. Giannis
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文献类型：
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作者：
J. Krieger;Toni Smeilus;Oliver Schackow;A. Giannis
报道了一种由(+)- wieland - micescher酮直接合成c -no - d- homo类固醇的方法。这种聚合合成策略利用可扩展的非对映选择性纳扎罗夫环化了手性芳基乙烯基酮，允许进一步功能化。在多克尺度上进行这种关键转化的能力为合成各种全新的C-nor-D-homo类固醇铺平了道路，而不需要经典的甾体类固醇重排或非手性线性反应序列。
A straightforward synthesis of C-nor-D-homo steroids starting from (+)-Wieland-Miescher ketone is reported. This convergent synthetic strategy utilizes a scalable diastereoselective Nazarov cyclization of functionalized chiral aryl vinyl ketones, allowing for further functionalization. The ability to conduct this key transformation on a multi-gram scale paves the way for the synthesis of a variety of completely new C-nor-D-homo steroids, without the need of a classic steran steroid rearrangement or achiral linear reaction sequences.