Synthesis of SHIP1-Activating Analogs of the Sponge Meroterpenoid Pelorol (pages 5195–5207)
Labros G. Meimetis, Matt Nodwell, Lu Yang, Xiaoxia Wang, Joyce Wu, Curtis Harwig, Grant R. Stenton, Lloyd F. Mackenzie, Thomas MacRury, Brian O. Patrick, Andrew Ming-Lum, Christopher J. Ong, Gerald Krystal, Alice L. -F. Mui and Raymond J. Andersen
Version of Record online: 3 AUG 2012 | DOI: 10.1002/ejoc.201200631
Two biomimetic routes have been used to synthesize analogs of the SHIP1-activating sponge meroterpenoid pelorol (1) in high ee. Resorcinol analog 18 is the most effective SHIP1-activating pelorol analog made to date and racemic 28·HCl, an amino analog, activates SHIP1 in vitro, and has effective antiinflammatory activity in a mouse model (ED50 ≈ 0.1 mg/kg).