Bioinspired total synthesis of agelastatin A.
A one-two punch: two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A. A diastereoselective C-ring formation, which proceeds through a 5-exo-trig cyclization or a Nazarov cyclization of a red-colored N-acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A.
Department of Chemistry, Texas A&M University, College Station, TX 77842-3012, USA.
Jeremy Chris P
JC
Reyes
Daniel
D
Romo
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis*; D058428:Silica Gel / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D003517:Cyclopentanes; D023303:Oxazolidinones; C464968:agelastatin A; D058428:Silica Gel