Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.
Chemistry. 2012 Jul 27;18(31):9601-11. doi: 10.1002/chem.201103604. Epub 2012 Jul 4.
A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon-carbon and carbon-heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl(3) as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone.
已经开发出一种针对靛红 A 全合成的策略，其中涉及几个晚期的金属催化转化，以解决关键的碳-碳和碳-杂原子键形成问题。作为该策略的一部分，通过使用 InCl(3) 作为催化剂或试剂，已经开发出将吲哚添加到靛红前体中，从而选择性地得到 2,2-二取代的 N-羟基吲哚啉-3-酮或 2,2-二取代的吲哚啉-3-酮化合物的方法。目前的方法提供了吲哚与靛红前体核加成的第一个实例。为了证明其可行性，已经从一种已知且易于获得的内酯完成了 13-脱氧靛红 A 的十步合成。
