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 synthesis
