Synthesis 2019; 51(24): 4601-4610
DOI: 10.1055/s-0039-1690025
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Enisorine D and its Analogues

Shashi Shashi
,
Mulla Althafh Hussain
,
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.

Supporting Information

 
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