Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (+/-)-platencin.
Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (+/-)-platencin.
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DOI：
10.1039/c004316h
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发表时间：
2010-09
影响因子：
3.2
通讯作者：
Vishwakarma Singh;B. Sahu;V. Bansal;S. Mobin
中科院分区：
文献类型：
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作者：
Vishwakarma Singh;B. Sahu;V. Bansal;S. Mobin
本文报道了从一个简单的芳香族前体合成Platencin的方法。芳香族化合物转化为反应性螺环氧环己-2，4-二烯酮和分子内环加成是我们方法的关键特征。用NaIO（4）氧化2-羟甲基-6-（3-羟基-己-5-烯基）-苯酚以得到二聚体，该二聚体在逆Diels-桤木反应后生成螺环氧环己-2，4-二烯酮，该螺环氧环己-2，4-二烯酮经历分子内Diels-桤木反应以在单一步骤中得到具有Platencin的核心结构和适当布置的官能团的三环加合物。还原存在于乙醇桥中的双键，操作环氧乙烷环并在六元环中引入双键，提供了已经转化为platencin的三环中间体。
A formal total synthesis of platencin from a simple aromatic precursor is described. Transformation of the aromatic compound into reactive spiroepoxycyclohexa-2,4-dienone and intramolecular cycloaddition are the key features of our methodology. 2-Hydroxymethyl-6-(3-hydroxy-hex-5-enyl)-phenol was oxidized with NaIO(4) to give a dimer that, upon a retro-Diels-Alder reaction, generated the spiroepoxycyclohexa-2,4-dienone that underwent intramolecular Diels-Alder reaction to give a tricyclic adduct having a core structure of platencin and appropriately disposed functional groups in a single step. Reduction of the double bond present in the ethano-bridge, manipulation of the oxirane ring and introduction of a double bond in the six-membered ring furnished a tricyclic intermediate which has already been converted into platencin.