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Skipped polyol is a common motif in numerous biologically significant polyketides and has been the focus of the development of novel synthetic methods and strategies. In this work, we devised a highly diastereoselective approach to access skipped triol(anti,syn-isomer) from a chiral α-allenic alcohol which was derived from kinetic resolution in our previous studies. An iodolactonization and subsequent radical deiodonation efficiently introduced the hydroxyl group at C3 in a highly diastereoselective manner and exemplified in enantioselective total synthesis of (+)-yashabushitriol.
In this work, we devised a highly diastereoselective approach to access skipped triol (anti, syn-isomer) from a chiral α-allenic alcohol which was derived from kinetic resolution in previous our previous studies. An iodolactonization and subsequent radical deiodonation efficiently delivered the hydroxyl group at C3 in a highly diastereoselective manner and in enantioselective total synthesis of (+) - yashabushitriol.