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Synthesis 2019; 51(24): 4601-4610
DOI: 10.1055/s-0039-1690025
DOI: 10.1055/s-0039-1690025
paper
Total Synthesis of Enisorine D and its Analogues
F.A.K. gratefully acknowledges the Science and Engineering Research Board, Department of Science and Technology, Government of India (EMR/2017/00348) for financial support. Shashi thanks the Department of Chemistry, Indian Institute of Technology Hyderabad. M.A.H. thanks the Council of Scientific and Industrial Research (CSIR), India.Further Information
Publication History
Received: 08 August 2019
Accepted after revision: 23 August 2019
Publication Date:
23 September 2019 (online)
Abstract
The first total synthesis of enisorine D, a natural product isolated from the marine sponge Iotrochota cf. iota, is described in 64% overall yield. The target molecule, which is an inhibitor of T3SS-dependent Yope secretion of Y. pseudotuberculosis, is achieved in seven linear steps from tyramine via simple and effective transformations that include bromination, acylation, alkylation, azidation, reduction and routine acid–amine coupling. A total of sixteen analogues are prepared by coupling with eight different cinnamic acids, two bromopyrrole carboxylic acids, five phenyl carboxylic acids and picolinic acid.
Key words
natural products - marine sponges - enisorines - bromination - acylation - reduction - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690025.
- Supporting Information
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