期刊
SYNTHESIS-STUTTGART
卷 51, 期 24, 页码 4601-4610出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690025
关键词
natural products; marine sponges; enisorines; bromination; acylation; reduction; total synthesis
资金
- Science and Engineering Research Board, Department of Science and Technology, Government of India [EMR/2017/00348]
- Department of Chemistry, Indian Institute of Technology Hyderabad
- Council of Scientific and Industrial Research (CSIR), India
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.
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