Original Mitsunobu-Triggered Sequence Involved in a One-Pot Domino Process toward Tetracyclic Systems Bearing a Bis-N,O-acetal Junction

摘要: Herein is reported an efficient, one-pot domino process through a 1,6-aza-Michael addition-triggered sequence and original Mitsunobu-type concerted for the synthesis of tetracyclic systems containing bis-N,O-acetal junction. This methodology led to construction four new bonds, cleavage three C–O generation asymmetric center. Mitsunobu activation afforded final ring closure involving creation two which remains unprecedented among sequences. The latter occurred in regioselective fashion at challenging C6-position 2-pyridone intermediates. In case adequately substituted enantiopure amino alcohols, up 95:5 diastereoisomeric excess was achieved. Computational studies allowed discrimination favored pathway supported regioselectivity as well diastereoselectivity observed this step.