Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.
作者： Katherine N. Fuhr , Danielle R. Hirsch , Ryan P. Murelli , Stacey E. Brenner-Moyer
DOI: 10.1021/ACS.ORGLETT.7B03196
关键词:
摘要: The first catalytic enantioselective [5 + 2] dipolar cycloaddition of a 3-hydroxy-4-pyrone-derived oxidopyrylium ylide is described. These studies leveraged the recently recognized ability dimers to serve as source ylide, which was found be key increasing yields and achieving enantiomeric excesses up 99%. General reaction conditions were identified for an array α,β-unsaturated aldehyde dipolarophiles. Reaction products possess four stereocenters, subsequent reduction introduced fifth contiguous stereocenter with total stereocontrol.
acs.org
figshare.com
sci-hub.se 参考文章(47)
Christine Meck, Noushad Mohd, Ryan P. Murelli, An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones. Organic Letters. ,vol. 14, pp. 5988- 5991 ,(2012) , 10.1021/OL302892G
Nahoko Uchiyama, Fumiyuki Kiuchi, Michiho Ito, Gisho Honda, Yoshio Takeda, Olimjon K Khodzhimatov, Ozodbek A Ashurmetov, None, New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi. Journal of Natural Products. ,vol. 66, pp. 128- 131 ,(2003) , 10.1021/NP020308Z
Girish Trivedi, Manikrao Salunkhe, Arun A. Yadav, Prajakta Sarang, A Practical Approach to Stereochemically Defined Tetrahydrofurans from [5+2] Oxidopyrylium-Alkene Cycloadducts Synlett. ,vol. 2007, pp. 0989- 0991 ,(2007) , 10.1055/S-2007-973866
Shunji Aoki, Yasuo Watanabe, Mami Sanagawa, Andi Setiawan, Naoyuki Kotoku, Motomasa Kobayashi, Cortistatins A, B, C, and D, Anti-angiogenic Steroidal Alkaloids, from the Marine Sponge Corticium simplex Journal of the American Chemical Society. ,vol. 128, pp. 3148- 3149 ,(2006) , 10.1021/JA057404H
Min Zhang, Na Liu, Weiping Tang, Stereoselective total synthesis of hainanolidol and harringtonolide via oxidopyrylium-based [5 + 2] cycloaddition. Journal of the American Chemical Society. ,vol. 135, pp. 12434- 12438 ,(2013) , 10.1021/JA406255J
K. C. Nicolaou, Qiang Kang, Sin Yee Ng, David Y.-K. Chen, Total synthesis of englerin A. Journal of the American Chemical Society. ,vol. 132, pp. 8219- 8222 ,(2010) , 10.1021/JA102927N
U. Murali Krishna, Kodand D. Deodhar, Girish K. Trivedi, Asymmetric oxidopyrylium-alkene [5+2] cycloaddition: a divergent approach for the synthesis of enantiopure oxabicyclo[5.4.0]undecanes Tetrahedron. ,vol. 60, pp. 4829- 4836 ,(2004) , 10.1016/J.TET.2004.04.003
Mohammed A Ali, Nirmala Bhogal, John BC Findlay, Colin WG Fishwick, None, The First de Novo-Designed Antagonists of the Human NK2 Receptor Journal of Medicinal Chemistry. ,vol. 48, pp. 5655- 5658 ,(2005) , 10.1021/JM050533O
Paul A. Wender, Frank E. McDonald, Studies on tumor promoters. 9. A second-generation synthesis of phorbol Journal of the American Chemical Society. ,vol. 112, pp. 4956- 4958 ,(1990) , 10.1021/JA00168A050
Noah Z. Burns, Michael R. Witten, Eric N. Jacobsen, Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions Journal of the American Chemical Society. ,vol. 133, pp. 14578- 14581 ,(2011) , 10.1021/JA206997E