A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin.
作者： Jothi L. Nallasivam , Rodney A. Fernandes
DOI: 10.1039/C6OB02398C
关键词: Methylenolactocin 、 Protecting group 、 Chemistry 、 Stereochemistry
摘要: A collective synthesis of a γ-butyrolactone class paraconic acids such as (+)-methylenolactocin, (+)-phaseolinic acid, (+)-nephrosteranic (+)-nephrosterinic (+)-rocellaric acid and (+)-protolichesterinic is described. The strategy adopted protecting-group-free based on efficient Pd-catalyzed Suzuki–Miyaura coupling Ru-catalyzed Sharpless oxidation to construct the core β-CO2H-γ-butyrolactone unit accomplish various acids.
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sci-hub.se 参考文章(87)
M. Mark midland, Alfonso tramontano, Aleksander kazubski, Richard S. graham, David J.S. tsai, Daniel B. cardin, Asymmetric reductions of propargyl ketones : An effective approach to the synthesis of optically-active compounds Tetrahedron. ,vol. 40, pp. 1371- 1380 ,(1984) , 10.1016/S0040-4020(01)82422-4
Venkati Bethi, Pullaiah Kattanguru, Rodney A. Fernandes, Domino Recombinant γ‐Isomerization and Reverse Wacker Oxidation of γ‐Vinyl‐γ‐butyrolactone: Synthesis of (+)‐trans‐, (–)‐ and (+)‐Disparlures European Journal of Organic Chemistry. ,vol. 2014, pp. 3249- 3255 ,(2014) , 10.1002/EJOC.201400021
Pradnya H. Patil, Rodney A. Fernandes, A stereoselective synthesis of the reported structure of polyporolide RSC Advances. ,vol. 5, pp. 49189- 49194 ,(2015) , 10.1039/C5RA07930F
Jothi L. Nallasivam, Rodney A. Fernandes, A Cascade Aza‐Cope/Aza‐Prins Cyclization Leading to Piperidine Derivatives European Journal of Organic Chemistry. ,vol. 2015, pp. 2012- 2022 ,(2015) , 10.1002/EJOC.201403607
J. Martin, P. C. Watts, Francis Johnson, A new method for the synthesis of α-methylenebutyrolactones J. Chem. Soc. D. ,vol. 0, pp. 27- 27 ,(1970) , 10.1039/C29700000027
Dipali A. Chaudhari, Pullaiah Kattanguru, Rodney A. Fernandes, A concise protecting-group-free synthesis of cephalosporolides E and F RSC Advances. ,vol. 5, pp. 42131- 42134 ,(2015) , 10.1039/C5RA06991B
Rodney A. Fernandes, Vijay P. Chavan, A 12-membered to a strained 11-membered ring: first stereoselective total synthesis of (−)-asteriscunolide C Chemical Communications. ,vol. 49, pp. 3354- 3356 ,(2013) , 10.1039/C3CC00316G
Barry M. Trost, Vince S. C. Yeh, Stereocontrolled Synthesis of (+)-Boronolide Organic Letters. ,vol. 4, pp. 3513- 3516 ,(2002) , 10.1021/OL026665I
Johann Mulzer, Lars Kattner, Achim R. Strecker, Christian Schroeder, Juergen Buschmann, Christian Lehmann, Peter Luger, Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer Journal of the American Chemical Society. ,vol. 113, pp. 4218- 4229 ,(1991) , 10.1021/JA00011A025
Yukio Masaki, Hideki Arasaki, Akichika Itoh, Enantiodivergent Synthesis of Both Enantiomeric Forms of Substituted Paraconic Acids Starting from D-Mannitol as a Chiral Pool. Tetrahedron Letters. ,vol. 40, pp. 4829- 4832 ,(1999) , 10.1016/S0040-4039(99)00855-2