Baran Phil S, Shenvi Ryan A
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.
J Am Chem Soc. 2006 Nov 1;128(43):14028-9. doi: 10.1021/ja0659673.
The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.
报道了以简洁的10步序列首次全合成（±）-chartelline C。完成这个历时数十年难题的亮点包括：（1）杂芳族卤素的化学和位置选择性安装；（2）炔烃连接基的卤素保留单还原；（3）放置敏感β-氯代烯酰胺的简单策略；（4）乙烯基羧酸异常容易的热解；（5）一种强大的环收缩反应，其在杂环化学中的潜在效用值得进一步研究。
