4.8 Article

A Modular Approach for Diversity-Oriented Synthesis of 1,3-trans-Disubstituted Tetrahydroisoquinolines: Seven-Step Asymmetric Synthesis of Michellamines B and C

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出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202205245

关键词

Diversity-Oriented Synthesis; Heterocycles; Naphthylisoquinoline Alkaloids; Tetrahydroisoquinolines; Total Synthesis

资金

  1. National Natural Science Foundation of China [21801193, 21871213, 22071189]
  2. Open Research Fund of State Key Laboratory of Bio-organic and Natural Products Chemistry [BNPC201109]
  3. Fundamental Research Funds for the Central Universities [2042021kf0214]
  4. Wuhan University

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This article presents a modular and convergent method for the rapid assembly of 1,3-trans-disubstituted THIQ frameworks, highlighting the broad synthetic utility of this approach in the synthesis of naphthylisoquinoline alkaloids.
1,3-trans-Disubstituted tetrahydroisoquinoline (THIQ) is a common heterocyclic structural unit of naphthylisoquinoline alkaloids. The assembly of this structural unit is not trivial, which constitutes a substantial challenge in the total synthesis of naphthylisoquinoline alkaloids and related pharmaceuticals. Herein, we report a modular and convergent method for the rapid assembly of 1,3-trans-disubstituted THIQ frameworks through a three-component Catellani reaction and a Au-I-catalyzed cyclization/reduction cascade. With widely available simple aryl iodides, aziridines and (triisopropylsilyl)acetylene as the building blocks, this method paves a practical way for the diversity-oriented synthesis of 1,3-trans-disubstituted THIQs. Based on this new method, concise syntheses of an analogue of the new drug mevidalen and four naphthylisoquinoline alkaloids have been accomplished, demonstrating the broad synthetic utility of this approach.

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