In this paper, we report a full account of the synthesis of dimeric hexahydropyrroloindole alkaloids and its analogues. The key feature of our new strategy is the novel catalytic copper (10 %) mediated intramolecular arylations of o-haloanilides followed by intermolecular oxidative dimerization of the resulting oxindoles in one pot. This sequential reaction leads to the key intermediates for the synthesis of (+)-chimonanthine, (+)-folicanthine, (-)-calycanthine and (-)-ditryptophenaline. In the presence of catalytic amount of cuprous iodide (10 %), an intramolecular arylation of o-haloanilides followed by an intermolecular oxidative dimerization of the resulting oxindoles leads to a common intermediate for the synthesis of (+)-chimonanthine, (+)-folicanthine and (-)-calycanthine. Based on this cascade sequence, we also developed a flexible strategy towards the asymmetric syntheses of dimeric HPI alkaloids (-)-ditryptophenaline and its analogues.

中文翻译：

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二聚 HPI 生物碱的全合成。


在本文中，我们报告了二聚六氢吡咯并吲哚生物碱及其类似物的合成的完整说明。我们新策略的关键特征是新型催化铜 (10%) 介导邻卤代苯胺的分子内芳基化，然后在一锅中对所得羟吲哚进行分子间氧化二聚。该连续反应产生了合成 (+)-chimonanthine、(+)-folicanthine、(-)-calycanthine 和 (-)-ditryptophenaline 的关键中间体。在催化量的碘化亚铜 (10%) 存在下，邻卤代苯胺发生分子内芳基化，随后所得羟吲哚发生分子间氧化二聚，生成 (+)-chimonanthine、(+)- 合成的常见中间体叶斑素和(-)-花萼甲素。基于该级联序列，我们还开发了一种灵活的策略来不对称合成二聚 HPI 生物碱 (-)-二色苯酚及其类似物。