Asymmetric total synthesis of (-)-alkaloid 223A and its 6-epimer

The Journal of Organic Chemistry
Xiaotao Pu, Dawei Ma

Abstract

The enantiopure gamma-amino alcohols 7 and 18 are prepared by using the diastereoselective Michael addition of lithium N-benzyl (R)-alpha-methylbenzylamide to alpha,beta-unsaturated esters as a key step. The Michael addition of 7 or 18 to an alkynone 8 followed by an intramolecular cyclization afford the cyclic enamine 10 or 20, which are subjected to the diastereoselective hydrogenation, and the subsequent transformations provide 6-epi-alkaloid 223A and alkaloid 223A, respectively.

References

Jan 1, 1997·Journal of Natural Products·H M GarraffoJ W Daly
May 10, 2002·Organic Letters·Naoki ToyookaTetsuo Kaneko

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Citations

Sep 11, 2009·Organic Letters·Partha GhoshJeffrey Aubé
Feb 3, 2007·Natural Product Reports·Joseph P Michael
May 24, 2011·Chemical Communications : Chem Comm·Adrien Quintard, Alexandre Alexakis
Jul 14, 2006·Organic Letters·Shanghai YuDawei Ma
Feb 26, 2005·Organic & Biomolecular Chemistry·Joseph P MichaelChristiaan W van der Westhuyzen
Jan 22, 2011·Chemistry, an Asian Journal·Weiwei ZiDawei Ma
Jul 16, 2010·Angewandte Chemie·Weiwei ZiDawei Ma
Dec 5, 2012·The Journal of Organic Chemistry·Nemai Saha, Shital K Chattopadhyay
Jun 7, 2012·Organic Letters·Pierre-Olivier DelayeJan Szymoniak
May 20, 2006·The Journal of Organic Chemistry·Renata Marcia de FigueiredoMathias Christmann
Aug 12, 2006·The Journal of Organic Chemistry·Xiaotao Pu, Dawei Ma
Oct 26, 2016·Bioorganic & Medicinal Chemistry·Christopher K ArnattYan Zhang

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