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

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
ABSTRACT

[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.

MATERIALS
Product Number
Brand
Product Description

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