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Double-Diels–Alder Approach to Maoecrystal V. Unexpected C–C Bond-Forming Fragmentations of the [2.2.2]-Bicyclic Core
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-14 00:00:00 , DOI: 10.1021/acs.orglett.7b02606 Brandon R. Smith 1 , Jon T. Njardarson 1
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-14 00:00:00 , DOI: 10.1021/acs.orglett.7b02606 Brandon R. Smith 1 , Jon T. Njardarson 1
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Synthetic studies toward maoecrystal V are reported. An oxidative dearomatization/Diels–Alder cascade to assemble the natural product carbocyclic core in one step is proposed. A facile electrocyclization is shown to suppress the intramolecular allene Diels–Alder pathway. This obstacle is alleviated via a stepwise approach with an allene equivalent to access the key cyclopentadiene-fused [2.2.2]-bicyclic core. Upon treatment with Lewis acid, the proposed intramolecular hetero-Diels–Alder reaction is cleanly and unexpectedly diverted either via C–C bond-forming fragmentation to the spiro-indene product (when R = OMe) or via elimination (when R = H).
中文翻译：
Double-Diels–Alder方法对Maoecrystal V. [2.2.2]-双环核的意外C–C键形成碎片
报道了对毛晶V的合成研究。提出了一种通过氧化脱芳香化/ Diels-Alder级联反应在一个步骤中组装天然产物碳环核的方法。研究表明，简单的电环化可以抑制分子内亚伦Diels-Alder途径。通过逐步使用异戊二烯来访问关键的环戊二烯稠合的[2.2.2]-双环核心，可以缓解此障碍。经路易斯酸处理后，拟议的分子内杂狄尔斯-阿尔德反应可通过C-C键形成的片段清晰地转移至螺-茚化合物（当R = OMe时）或通过消除（当R = H时） 。
更新日期：2017-09-14
中文翻译：
Double-Diels–Alder方法对Maoecrystal V. [2.2.2]-双环核的意外C–C键形成碎片
报道了对毛晶V的合成研究。提出了一种通过氧化脱芳香化/ Diels-Alder级联反应在一个步骤中组装天然产物碳环核的方法。研究表明，简单的电环化可以抑制分子内亚伦Diels-Alder途径。通过逐步使用异戊二烯来访问关键的环戊二烯稠合的[2.2.2]-双环核心，可以缓解此障碍。经路易斯酸处理后，拟议的分子内杂狄尔斯-阿尔德反应可通过C-C键形成的片段清晰地转移至螺-茚化合物（当R = OMe时）或通过消除（当R = H时） 。
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