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.
Methot
Joey L
JL
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Roush
William R
WR
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