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Total Synthesis of Dimeric HPI Alkaloids

Author:
Shen, Xianfu, Zhou, Yongyun, Xi, Yongkai, Zhao, Jingfeng, Zhang, Hongbin
Source:
Nat. Prod. Bioprospect. 2016 v.6 no.2 pp. 117-139
ISSN:
2192-2195
Subject:
alkaloids, arylation, copper, dimerization, iodides
Abstract:
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.
Agid:
5165007