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Diastereoselective Formation of Tetrahydrofurans via Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of the C13–C29 Subunit of Amphidinolide N

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journal contribution
posted on 16.11.2012, 00:00 by Barry M. Trost, Jullien Rey
An efficient synthesis of the C13–C29 fragment of amphidinolide N is described. The synthesis relies on a new strategy involving Pd-catalyzed asymmetric allylic alkylation to generate diastereoselectively the cis- or trans-THF unit simply by varying the enantiomer of the ligand. The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer.