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Synthetic studies toward FR182877. Remarkable solvent effect in the vinylogous morita-baylis-hillman cyclization.

Organic letters (2003-10-24)
Joey L Methot, William R Roush
RÉSUMÉ

[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.

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Sigma-Aldrich
Trimethylphosphine, 97%
Sigma-Aldrich
Trimethylphosphine solution, 1.0 M in THF
Sigma-Aldrich
Trimethylphosphine solution, 1.0 M in toluene