Haliclonin A (1) is a macrocyclic alkaloid isolated in 2009 from a marine sponge Haliclona sp. collected from Korean waters by Shin and co-workers. Haliclonin A (1) contains two aza-macrocycles and is structurally related to sarains A-C, but possessing an unprecedented 3-azabicyclononane framework. Preliminary bioassay showed that this unique natural product exhibited moderate antibacterial activity against several microbial strains, and cytotoxicity against the K562 leukemia cell line with an IC50 of 15.9 mg/ mL. Despite its intriguing structure and interesting bioactivities, no total synthesis of haliclonin A (1) has been reported to date. In 2016, we acomplished first total synthesis of the alkaloid (-)-haliclonin A.

Enantioselective total synthesis of the alkaloid (-)-haliclonin A

254th National Meeting (2017)

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