Heterocyclic Compounds
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ChemInform Abstract: An Optically Active Allene Macrodiolide: A Versatile Key Intermediate Leading to (-)-Pyrenophorin and (+)-Dibenzomacrodiolides.
First published: May 30, 1989
Abstract
The key step in the synthesis of the allene macrodiolides (VII) is the dimerization of the ω-chlorocarbonylphosphonium bromides (VI) via olefination of the intermediately formed ketones.
ChemInform Abstract
The key step in the synthesis of the allene macrodiolides (VII) is the dimerization of the ω-chlorocarbonylphosphonium bromides (VI) via olefination of the intermediately formed ketones. The cyclic dimers (VII) are accompanied by minor amounts of tri- and tetramers depending on the concentration of the solution and the chain length of (VI). The diastereomers (VIIa) are separated by chromatographic methods and then employed as synthetic precursors of chiral macrolides, e.g. (VIII) and (IX).
