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- “Intramolecular Diels-Alder reactions using chiral ruthenium Lewis acids and application in the total synthesis of ent-ledol”
S. Thamapipol, E.P. Kündig,
Org. Biomol. Chem. 2011, 9, 7564-7570.
One-point binding chiral ruthenium Lewis acids incorporating the C2-symmetric electron-poor bidentate phosphinite ligand BIPHOP-F and a Cp or an indenyl ‘roof’ can efficiently catalyze asymmetric intramolecular Diels-Alder reactions of trienes to form bicyclic adducts with good to excellent asymmetric induction. This reaction forms the key step in a total synthesis of ent-ledol in 96% ee. The synthesis also helps to clarify the stereochemical assignment of ledol and inconsistencies in the measured optical rotation.
DOI : 10.1039/C1OB06121F
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