Concise and Scalable Total Syntheses of Lamellarin Z and other Natural Lamellarins: Regiocontrolled Assembly of the Central Pyrrole Core and Cross Dehydrogenative Coupling Enroute to the Pentacyclic Coumarin-Pyrrole-Isoquinoline Scaffold 

  1. Virendra Kumar,
  2. Abdus Salam,
  3. Dileep Kumar and
  4. Tabrez KhanORCID Logo

Submitting author affiliation: Indian Institute of Technology Bhubaneswar, Khurdha, India

Beilstein Arch. 2020, 202087. doi:10.3762/bxiv.2020.87.v1

Published 29 Jul 2020

  • Preprint

Abstract

An efficient construction of the central 1,2,4-trisubstituted pyrrole core via one-pot [3+2] cycloaddition/elimination/aromatization sequence-based domino process and subsequent Pd-mediated cross dehydrogenative coupling between the C-H bonds of pyrrole and the peripheral aryl rings enables rapid access to the pentacyclic coumarin-pyrrole-isoquinoline scaffolds which were smoothly elaborated to the targeted lamellarins alkaloids. The total synthesis of lamellarins Z and S with the highest overall yield reported till date, besides the synthesis of several other natural lamellarins have been realized in 5-6 steps with overall yields ranging from 20-27%.

Keywords: aziridine; cross-dehydrogenative coupling; domino process; lamellarins; total synthesis

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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Kumar, V.; Salam, A.; Kumar, D.; Khan, T. Beilstein Arch. 2020, 202087. doi:10.3762/bxiv.2020.87.v1

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