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Racemization-free Synthesis Of (S)-(+)-tylophorine From L-proline By Radical Cyclization.

Alexander Stoye, T. Opatz
Published 2010 · Chemistry, Medicine

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The phenanthroindolizidine alkaloid (S)-(+)-tylophorine was synthesized from L-proline in nine linear steps including a double bromination and a free-radical cyclization of an N-aziridinylimine as the key steps. The phenanthrene moiety was prepared from homoveratric acid and veratraldehyde and permits the variation of each oxygen-substituted ring.



This paper is referenced by
10.1039/C5QO00361J
Iodine(III)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes
Christian Depken (2016)
10.1016/J.TET.2013.02.014
Concise synthesis of tylophorine
Qi-xian Lin (2013)
10.1021/acs.joc.6b01161
Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization.
G. Liu (2016)
10.1021/np300838w
Left, right, or both? On the configuration of the phenanthroindolizidine alkaloid tylophorine from Tylophora indica.
A. Stoye (2013)
10.1016/j.bmcl.2012.03.109
Synthesis of indolizidinone analogues of cytotoxic alkaloids: monocyclic precursors are also active.
A. Boto (2012)
10.1039/C4QO00084F
Asymmetric synthesis of (S)-tylophorine and (S)-cryptopleurine via one-pot Curtius rearrangement and Friedel–Crafts reaction tandem sequence
F. Chen (2014)
10.1039/c4ob00200h
An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence.
Bo Su (2014)
10.1002/EJOC.201800908
The Reactivity of Enantiopure (S)‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions
P. Šafár̆ (2018)
10.1021/jo3011045
A five-step synthesis of (±)-tylophorine via a nitrile-stabilized ammonium ylide.
G. Lahm (2012)
10.1021/jo302725q
An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence.
Bo Su (2013)
10.1039/C3RA47465H
Total synthesis of phenanthroindolizidine alkaloids via asymmetric deprotonation of N-Boc-pyrrolidine
Meng Deng (2014)
10.1016/B978-0-444-63929-5.00002-4
Advances in the Chemistry of Natural and Semisynthetic Topoisomerase I/II Inhibitors
V. D’yakonov (2017)
10.1002/EJOC.201201472
The First Enantioselective Approach to 13a‐Methyl‐14‐hydroxyphenanthroindolizidine Alkaloids – Synthetic Studies towards Hypoestestatin 2
Bo Su (2013)
10.1021/ja300807e
Nature-inspired total synthesis of (-)-fusarisetin A.
Jing Xu (2012)
10.1016/J.TETLET.2013.10.124
Total synthesis of (±)-antofine
Ming Yi (2014)
10.1039/c4ob01133c
Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines.
Cintia Anton-Torrecillas (2014)
10.1021/acs.joc.6b00507
Intramolecular Dehydrogenative Coupling of 2,3-Diaryl Acrylic Compounds: Access to Substituted Phenanthrenes.
V. Gupta (2016)
10.1002/EJOC.201403700
Synthesis of (–)‐Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization
Alexander Stoye (2015)
10.1002/HLCA.201200564
Directed MetalationCross‐Coupling Strategies. Total Syntheses of the Alleged and the Revised Phenanthrene Natural Product Gymnopusin
Xin Wang (2012)
10.1248/YAKUSHI.16-00202
Efficient Synthesis of Polyaromatic Hydrocarbon via a Formal [2+2] Cycloaddition.
Y. Yamaoka (2016)
10.1039/C3RA44193H
Recent advances in the synthesis of naturally occurring pyrrolidines, pyrrolizidines and indolizidine alkaloids using proline as a unique chiral synthon
Chinmay Bhat (2014)
10.1016/J.TETLET.2018.04.052
Total synthesis of (R)-tylophorine by using an asymmetric hydrogenation of the allyl alcohol
Rui Li (2018)
10.1021/JO3012122
Enantioselective approach to 13a-methylphenanthroindolizidine alkaloids.
Bo Su (2012)
10.1002/ADSC.201100578
A Novel Sodium Nitrite-Catalyzed Oxidative Coupling for Constructing Polymethoxyphenanthrene Rings
Bo Su (2012)
10.1002/SLCT.201803529
Enantioselective Synthesis of (R)‐Antofine and (R)‐Cryptopleurine
Anas Ansari (2018)
10.2174/1568026613666131213154633
Synthesis of alkaloids: recent advances in the synthesis of phenanthroindolizidine alkaloids.
A. Burtoloso (2014)
10.1002/ejoc.202000391
Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors
J. Bonjoch (2020)
10.1002/chem.201403442
Oxidative cyclization reaction of 2-aryl-substituted cinnamates to form phenanthrene carboxylates by using MoCl5.
Kathrin Wehming (2014)
10.1021/jo500013e
Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary.
Yanlong Zheng (2014)
10.1016/j.bmc.2012.07.044
Synthesis and evaluation of the anti-proliferative and NF-κB activities of a library of simplified tylophorine analogs.
M. J. Niphakis (2012)
10.1016/B978-0-08-097742-3.00419-5
4.13 Radical Cyclizations and Sequential Radical Reactions
B. M. Loertscher (2014)
10.1038/s41598-017-17015-8
Total synthesis of the reported structure of 13a-hydroxytylophorine
Hui Bin Zhang (2017)
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