Diels–Alder Based Approach to Prenyleudesmane Diterpenoids

A Versatile, Diels–Alder Reaction-Based Approach to Prenyleudesmane Diterpenoids: A Concise Total Synthesis of Sinupol: K. Ota, K. Kamaike, H. Miyaoka
Synlett 2020, 31, DOI: 10.1055/s-0037-1610757


Protein Tyrosine Phosphatase 1B (PTP1B) is an important emerging target in type 2 diabetes therapy, as it plays a key role in insulin signaling. Several PTP1B inhibitors are currently being evaluated in the clinics. The natural marine compound sinupol – belonging to the family of prenyleudesmane diterpenoids – has shown micromolar inhibitory PTP1B capacity and represents an interesting target in this context. Recently, the group of Professor Hiroaki Miyaoka from the Tokyo University of Pharmacy and Life Sciences (Japan) has described a new synthetic approach to sinupol.


Professor Miyaoka said: “A concise total synthesis of sinupol, a PTP1B inhibitory active prenyleudesmane diterpenoid, was achieved by using Evans asymmetric alkylation to construct the stereocenter and an intramolecular Diels–Alder reaction to build up the trans-fused decalin as the key steps.”

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