Formal total synthesis of (-)-apicularen a via transannular conjugate addition
Formal total synthesis of (-)-apicularen a via transannular conjugate addition
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DOI：
10.1021/ol0497943
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发表时间：
2004-04-15
期刊：
影响因子：
5.2
通讯作者：
Rizzacasa, MA
中科院分区：
文献类型：
--
作者：
Hilli, F;White, JM;Rizzacasa, MA
本文报道了粘细菌代谢产物（-）-apicularen A（1）的全合成。关键步骤涉及新的酸介导的C13羟基到大环内酯5a或5 b中的α，β-不饱和酮中的跨环共轭加成，以提供相同的反式吡喃酮4。将4转化为已知的apicularen中间体二醇3完成了形式合成。
The formal total synthesis of the myxobacteria metabolite (-)-apicularen A (1) is described. The key step involved a novel acid-mediated transannular conjugate addition of the C13 hydroxyl into the alpha,beta-unsaturated ketone in either of the macrolactones 5a or 5b to provide the same trans-pyranone 4. Conversion of 4 into the known apicularen intermediate diol 3 completed the formal synthesis.