Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 21, Pages 7564-7570Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06121f
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Funding
- Swiss National Science Foundation
- University of Geneva
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One-point binding chiral ruthenium Lewis acids incorporating the C-2-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.
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