Total synthesis of irciniastatin A (Psymberin).
The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.
Crimmins
Michael T
MT
Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Stevens
Jason M
JM
Schaaf
Gregory M
GM
D002384:Catalysis; D003374:Coumarins; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003374:Coumarins; D011753:Pyrones; C498383:psymberin