Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B.
The asymmetric total syntheses of (-)-agelastatin A and (-)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish a key functionalized cyclopentene intermediate. Selective bromination in the final step led to either agelastatin A or agelastatin B, depending upon conditions.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Saunders
Joe C
JC
D000470:Alkaloids; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009861:Onium Compounds / Q000737:chemistry*; D023303:Oxazolidinones
D000470:Alkaloids; D007202:Indicators and Reagents; D009861:Onium Compounds; D023303:Oxazolidinones; C464968:agelastatin A; C464967:agelastatin B