Journal article

Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment

Sadegh Shabani, Jonathan M White, Craig A Hutton

Organic Letters | AMER CHEMICAL SOC | Published : 2020

Abstract

The total synthesis of the putative structure of asperipin-2a is described. The synthesis features ether cross-links between the phenolic oxygen of Tyr6 and the β position of Tyr3 and the phenolic oxygen of Tyr3 and the β position of Hpp1 in the unique 17- and 14-membered bicyclic structure of asperipin-2a, respectively. The synthesized putative structure does not match the natural product, and a stereochemical reassignment is postulated.

Grants

Awarded by Australian Research Council


Funding Acknowledgements

This project was funded by the Australian Research Council (DP180101804). S.S. thanks the University of Melbourne for a Melbourne Research Scholarship (MRS) and an Award from the Albert Shimmins Fund. We thank Prof. Oikawa (Hokkaido University) for the provision of a sample of natural asperipin2a.