Synthetic studies toward FR182877. Remarkable solvent effect in the vinylogous morita-baylis-hillman cyclization.
[reaction: see text]. The intramolecular vinylogous Morita-Baylis-Hillman reaction was explored to access the central cyclopentane ring of FR182877. The reaction manifold and product distribution is strikingly solvent and substrate dependent.
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Joey L
JL
Methot
William R
WR
Roush
D002384:Catalysis; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*
C408303:FR 182877; D009947:Organotin Compounds; D010720:Phosphines; D011083:Polycyclic Compounds; D012997:Solvents; C099734:vinyltributylstannane; C049750:trimethyl phosphine