TotalSynthesisof(-)-Quinocarcin.ppt

* Total Synthesis of (-)-Quinocarcin Stoltz. J. Am. Chem. Soc., 2008, 130 (51), 17270-17271 Myers. J. Am. Chem. Soc., 2005, 127 (48), 16796-16797 Zhu. J. Am. Chem. Soc., 2008, 130 (22), 7148-7152 李楠 2009.04.20 inhibition of lung cancer activity against lymphocytic leukemia etc. intramolecular nucleophilic attack intermolecular condensation Pictet-Spengler reaction alkylation install the labile oxazolidine ring effectively obviated the regioselectivity mixture of two diastereomers (ratio 3/2) Strong nucleophile weak nucleophile E/Z = 8/1 deprotection under one-pot condition Stoltzs total synthesis of (-)-Quinocarcin auxiliary-controlled dipolar cycloaddition Screened Zn(OTf)2, Sc(OTf)3, and Sm(OTf)3, and none provided enamine 11 in greater than 40% yield. aryen annulation reaction Selectively condensed 10% overall yield 11 steps (shortest synthesis to date) *