Synthetic studies toward the zoanthamine alkaloids: synthesis of the fully functionalized BC ring motif

Synthetic studies toward the zoanthamine alkaloids: synthesis of the fully functionalized BC ring motif
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DOI:
10.1016/j.tetlet.2005.06.037
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发表时间:
2005-08-08
影响因子:
1.8
通讯作者:
Theodorakis, EA
Theodorakis, EA
中科院分区:
化学4区
文献类型:
--
作者:
Rivas, F;Ghosh, S;Theodorakis, EA

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一种合成方法,对内酯20,代表了完全官能化的BC环基序的zoanthamine生物碱,已开发,并在此提出。具有挑战性的C9季中心20通过烯酮17的威尔金森氢化,随后构建(X)-溴缩醛和仅从BC环系统的α面进行分子内环化来安装。(c)2005爱思唯尔有限公司保留所有权利。
A synthetic approach toward lactone 20, representing the fully functionalized BC ring motif of the zoanthamine alkaloids, has been developed and is presented herein. The challenging C9 quaternary center of 20 was installed by a Wilkinson hydrogenation of enone 17 followed by construction of an (x-bromo acetal and intramolecular cyclization exclusively from the alpha face of the BC ring system. (c) 2005 Elsevier Ltd. All rights reserved.