The total synthesis of the synoxazolidinones, recently isolated from the sub-Artic ascidian Synoicum pulmonaria, has been accomplished. The rapid assembly of these bioactive natural products was made possible by an imine acylation/enol addition cascade that installs the (Z)-alkene and 4-oxazolidinone in a single transformation. Biological evalation of these natural products has confirmed thier antimicrobial activity and novel analogues have provided lead compounds for further study.

Rapid construction of 4-oxazolidinones: Total synthesis of the synoxazolidinone family of antimicrobial natural products

245th National Meeting (2013)

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