Efficient oxa-Diels-Alder/semipinacol rearrangement/aldol cascade reaction: short approach to polycyclic architectures.
Efficient oxa-Diels-Alder/semipinacol rearrangement/aldol cascade reaction: short approach to polycyclic architectures.
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DOI：
10.1021/acs.orglett.5b00125
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发表时间：
2015-02
期刊：
影响因子：
5.2
通讯作者：
Jin‐Bao Peng;Yue Qi;Ze-Ran Jing;Shao-Hua Wang;Y. Tu;Dao-Yong Zhu;Fu‐Min Zhang
中科院分区：
文献类型：
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作者：
Jin‐Bao Peng;Yue Qi;Ze-Ran Jing;Shao-Hua Wang;Y. Tu;Dao-Yong Zhu;Fu‐Min Zhang
在SnCl4的促进下，建立了一种新的碳亲电试剂诱导的烯丙基硅醚与β，γ-不饱和α-酮酯的分子间oxa- diols - alder /半品萘醇重排/醛醇级联反应。这种高效的转化可以在一次操作中快速构建多达五个连续立体中心的多环结构，具有中等到良好的产率和高非对映选择性，并将为许多生物学上重要的多环天然产物的框架和/或类似物提供通用的短方法。
A novel carbon electrophile induced intermolecular oxa-Diels-Alder/semipinacol rearrangement/aldol cascade reaction of allylic silyl ether with β,γ-unsaturated α-ketoester has been developed under the promotion of SnCl4. This highly efficient transformation enables the quick construction of polycyclic architectures with up to five contiguous stereogenic centers in a single operation with moderate to good yields as well as high diastereoselectivity and would provide versatile short approaches to frameworks and/or analogues of numerous biologically important polycyclic natural products.