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Journal articles on the topic 'Octahydroindoles'

Author: Grafiati

Published: 3 June 2025

Last updated: 31 July 2025

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1

Yan, Jiahang, Wenting Zhang, Qiaoqiao He та ін. "Enantioselective direct vinylogous Michael addition for constructing enantioenriched γ,γ-dialkyl substituted butyrolactams and octahydroindoles". Organic & Biomolecular Chemistry 20, № 12 (2022): 2387–91. http://dx.doi.org/10.1039/d2ob00112h.

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A nickel(ii)/chiral N,N′-dioxide catalyzed asymmetric direct vinylogous Michael addition of unsaturated butyrolactams enables synthesizing enantioenriched γ,γ-dialkyl substituted butyrolactams and octahydroindoles.

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2

Hanessian, Stephen, Stéphane Dorich, and Juan Del Valle. "Synthesis of Functionalized Octahydroindoles Related to Daphnyphyllum Alkaloids." Synlett 25, no. 06 (2014): 799–804. http://dx.doi.org/10.1055/s-0033-1340794.

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3

Coldham, Iain, Katherine M. Crapnell, Jonathan D. Moseley, and Rémi Rabot. "Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (2001): 1758–63. http://dx.doi.org/10.1039/b104390k.

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4

Mena, Marisa, Josep Bonjoch, Domingo Gomez Pardo, and Janine Cossy. "Ring Expansion of Functionalized Octahydroindoles to Enantiopurecis-Decahydroquinolines†." Journal of Organic Chemistry 71, no. 16 (2006): 5930–35. http://dx.doi.org/10.1021/jo060592p.

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5

Ghirardi, Elena, Rosa Griera, Miriam Piccichè, et al. "Stereocontrolled Access to Enantiopure 7-Substituted cis- and trans-Octahydroindoles." Organic Letters 18, no. 22 (2016): 5836–39. http://dx.doi.org/10.1021/acs.orglett.6b02861.

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6

Coldham, Iain, Katherine M. Crapnell, Jonathan D. Moseley, and Remi Rabot. "ChemInform Abstract: Intramolecular Azomethine Ylide Cycloaddition Reactions to Give Octahydroindoles." ChemInform 32, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.200152110.

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7

Dorich, Stephane, Juan R. Del Valle, and Stephen Hanessian. "ChemInform Abstract: Synthesis of Functionalized Octahydroindoles Related to Daphnyphyllum Alkaloids." ChemInform 45, no. 38 (2014): no. http://dx.doi.org/10.1002/chin.201438112.

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8

Reimann, Eberhard, Christian Ettmayr, and Kurt Polborn. "Angularly Substituted Octahydroindoles, Decahydroquinolines, Octahydropyrindines, and Octahydrocyclopenta[b]pyrroles by Bruylants Reaction." Monatshefte f�r Chemie / Chemical Monthly 135, no. 5 (2004): 557–79. http://dx.doi.org/10.1007/s00706-003-0136-8.

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9

Gravier-Pelletier, Christine, William Maton, Gildas Bertho, and Yves Le Merrer. "Synthesis and glycosidase inhibitory activity of enantiopure polyhydroxylated octahydroindoles and decahydroquinolines, analogs to castanospermine." Tetrahedron 59, no. 44 (2003): 8721–30. http://dx.doi.org/10.1016/j.tet.2003.09.044.

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10

Basch, Corey H., Jameson A. Brinck, Joaquin E. Ramos, Stephen A. Habay, and Glenn P. A. Yap. "Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar Cycloaddition of 2-Acyl-5-aminooxazolium Salts." Journal of Organic Chemistry 77, no. 22 (2012): 10416–21. http://dx.doi.org/10.1021/jo301600p.

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11

Parra, Claudio, Caroline Bosch, Enrique Gómez-Bengoa, Josep Bonjoch, and Ben Bradshaw. "Asymmetric Synthesis of Octahydroindoles via a Domino Robinson Annulation/5-Endo Intramolecular Aza-Michael Reaction." Journal of Organic Chemistry 81, no. 21 (2016): 10172–79. http://dx.doi.org/10.1021/acs.joc.6b01568.

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12

Cui, Yi, Samantha Kwok, Andrew Bucholtz, Boyd Davis, Ralph A. Whitney, and Philip G. Jessop. "The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage." New Journal of Chemistry 32, no. 6 (2008): 1027. http://dx.doi.org/10.1039/b718209k.

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13

Han, Yong, Bo Zheng та Yungui Peng. "Construction of Chiral 2-Substituted Octahydroindoles from Cyclic Ketones and Nitroolefins Bearing only One α-Substituent". Advanced Synthesis & Catalysis 357, № 6 (2015): 1136–42. http://dx.doi.org/10.1002/adsc.201400851.

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14

Mokotoff, Michael, and Scott T. Hill. "Azabicyclo chemistry.7. Ultra-high field (600 MHz) NMR spectroscopy in solving conformational problems: cis-Octahydroindoles." Journal of Heterocyclic Chemistry 25, no. 1 (1988): 65–71. http://dx.doi.org/10.1002/jhet.5570250110.

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15

Basch, Corey H., Jameson A. Brinck, Joaquin E. Ramos, Stephen A. Habay, and Glenn P. A. Yap. "ChemInform Abstract: Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar Cycloaddition of 2-Acyl-5-aminooxazolium Salts." ChemInform 44, no. 16 (2013): no. http://dx.doi.org/10.1002/chin.201316075.

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16

Clarisse, Damien, Bernard Fenet, and Fabienne Fache. "Hexafluoroisopropanol: a powerful solvent for the hydrogenation of indole derivatives. Selective access to tetrahydroindoles or cis-fused octahydroindoles." Organic & Biomolecular Chemistry 10, no. 32 (2012): 6587. http://dx.doi.org/10.1039/c2ob25980j.

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17

Han, Yong, Bo Zheng та Yungui Peng. "ChemInform Abstract: Construction of Chiral 2-Substituted Octahydroindoles from Cyclic Ketones and Nitroolefins Bearing only One α-Substituent." ChemInform 46, № 33 (2015): no. http://dx.doi.org/10.1002/chin.201533035.

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18

Wales, Steven M., Holly V. Adcock, William Lewis, Daniel Hamza, and Christopher J. Moody. "Nitrogen-Bridged, Natural Product Like Octahydrobenzofurans and Octahydroindoles: Scope and Mechanism of Bridge-Forming Reductive Amination via Caged Heteroadamantanes." European Journal of Organic Chemistry 2018, no. 34 (2018): 4696–704. http://dx.doi.org/10.1002/ejoc.201800962.

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19

Hanessian, Stephen, Martin Tremblay, and Jens F. W. Petersen. "TheN-Acyloxyiminium Ion Aza-Prins Route to Octahydroindoles: Total Synthesis and Structural Confirmation of the Antithrombotic Marine Natural Product Oscillarin." Journal of the American Chemical Society 126, no. 19 (2004): 6064–71. http://dx.doi.org/10.1021/ja030669g.

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20

Kubyshkin, Vladimir, and Nediljko Budisa. "Construction of a polyproline structure with hydrophobic exterior using octahydroindole-2-carboxylic acid." Organic & Biomolecular Chemistry 15, no. 3 (2017): 619–27. http://dx.doi.org/10.1039/c6ob02306a.

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21

Sanchez, Ignacio H., Maria Isabel Larraza, Irma Rojas, et al. "2D NMR Studies of Octahydroindole Svstems." Spectroscopy Letters 20, no. 2 (1987): 125–47. http://dx.doi.org/10.1080/00387018708081534.

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22

Chiha, Slim, Matthias Spilles, Jörg-Martin Neudörfl, and Hans-Günther Schmalz. "A Stereoselective Synthesis of the ACE Inhibitor Trandolapril." Synlett 30, no. 07 (2019): 813–16. http://dx.doi.org/10.1055/s-0037-1612306.

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A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l-pyroglutamic acid derivative, a highly diastereoselective Hosomi–Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

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23

Sydnes, Magne O., Phuc Van Le, Jens Olschimke, et al. "Synthesis of two chiral octahydroindole scaffolds for drug discovery." Tetrahedron 72, no. 9 (2016): 1225–28. http://dx.doi.org/10.1016/j.tet.2016.01.018.

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24

Kalaitzakis, Dimitris, Myron Triantafyllakis, Georgios I. Ioannou, and Georgios Vassilikogiannakis. "One-Pot Transformation of Simple Furans into Octahydroindole Scaffolds." Angewandte Chemie 129, no. 14 (2017): 4078–81. http://dx.doi.org/10.1002/ange.201700620.

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25

Kalaitzakis, Dimitris, Myron Triantafyllakis, Georgios I. Ioannou, and Georgios Vassilikogiannakis. "One-Pot Transformation of Simple Furans into Octahydroindole Scaffolds." Angewandte Chemie International Edition 56, no. 14 (2017): 4020–23. http://dx.doi.org/10.1002/anie.201700620.

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26

Reid, Joel W., James A. Kaduk, and Martin Vickers. "The crystal structure of trandolapril, C24H34N2O5: an example of the utility of raw data deposition in the powder diffraction file." Powder Diffraction 31, no. 3 (2016): 205–10. http://dx.doi.org/10.1017/s0885715616000294.

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The crystal structure of trandolapril has been solved by parallel tempering using the FOX software package with laboratory powder diffraction data submitted to and published in the Powder Diffraction File. Rietveld refinement was performed with the software package GSAS yielding orthorhombic lattice parameters of a = 19.7685(4), b = 15.0697(4), and c = 7.6704(2) Å (C24H34N2O5, Z = 4, space group P212121). The Rietveld refinement results were compared with density functional theory (DFT) calculations performed with CRYSTAL14. While the structures are similar, discrepancies are observed in the c

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27

Liu, Jiameng, Mengli Zhang, Zhenkuai Huang, et al. "Diversity, Biosynthesis and Bioactivity of Aeruginosins, a Family of Cyanobacteria-Derived Nonribosomal Linear Tetrapeptides." Marine Drugs 21, no. 4 (2023): 217. http://dx.doi.org/10.3390/md21040217.

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Aeruginosins, a family of nonribosomal linear tetrapeptides discovered from cyanobacteria and sponges, exhibit in vitro inhibitory activity on various types of serine proteases. This family is characterized by the existence of the 2-carboxy-6-hydroxy-octahydroindole (Choi) moiety occupied at the central position of the tetrapeptide. Aeruginosins have attracted much attention due to their special structures and unique bioactivities. Although many studies on aeruginosins have been published, there has not yet been a comprehensive review that summarizes the diverse research ranging from biogenesi

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28

Barakat, Assem, Saeed Alshahrani, Abdullah Mohammed Al-Majid, et al. "Synthesis of a New Class of Spirooxindole–Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors." Molecules 25, no. 20 (2020): 4671. http://dx.doi.org/10.3390/molecules25204671.

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A series of new oxindole-based spiro-heterocycles bearing the benzo[b]thiophene motif were synthesized via a 1,3-dipolar cycloaddition reaction and their acetylcholinesterase (AChE) inhibitory activity was evaluated. All the synthesized compounds exhibited moderate inhibitory activities against AChE, while IIc was found to be the most active analog with an IC50 value of 20,840 µM·L−1. Its molecular structure was a 5-chloro-substituted oxindole bearing benzo[b]thiophene and octahydroindole moieties. Based on molecular docking studies, IIc was strongly bound to the catalytic and peripheral anion

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29

King, Frank D. "A novel synthesis of (±)-harmacine and (±)1,2,3,4,6,7,12,12b-octahydroindole[2,3-a]quinolizine." Journal of Heterocyclic Chemistry 44, no. 6 (2007): 1459–63. http://dx.doi.org/10.1002/jhet.5570440634.

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30

Tompkins, David C., Laurence W. Reilly, Randall B. Nelson, Lloyd J. Dolby, and Gordon W. Gribble. "Synthesis of 6-Oxo-1,2,3,4,6,7,12,12b -octahydroindolo[2,3-a ]quinolizine." Journal of Heterocyclic Chemistry 55, no. 4 (2018): 1048–52. http://dx.doi.org/10.1002/jhet.3130.

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31

Tompkins, David C., Randall B. Nelson, Lloyd J. Dolby, and Gordon W. Gribble. "Synthesis of 7-Oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a ]quinolizine." Journal of Heterocyclic Chemistry 55, no. 9 (2018): 2168–71. http://dx.doi.org/10.1002/jhet.3251.

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32

Alshahrani, Saeed, Abdullah Mohammed Al-Majid, Abdullah Saleh Alamary, Mar Ríos-Gutiérrez, and Assem Barakat. "Exploring Regio- and Stereoselectivity in [3+2] Cycloaddition: Molecular Electron Density Theory Approach for Novel Spirooxindole-Based Benzimidazole with Pyridine Spacer." Crystals 13, no. 7 (2023): 1085. http://dx.doi.org/10.3390/cryst13071085.

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A new ethylene derivative was synthesized as a precursor for the [3+2] cycloaddition (32CA) reaction to access a novel spirooxindole embodied with benzimidazole with a pyridine spacer. The chalcone derivatives 3a–j is obtained with condensation of the acetyl derivative with aryl aldehydes. The one-pot multi-component reaction of the ethylene derivative, 5-Cl-isatin, and octahydroindole-2-carboxylic acid enables the construction of a highly functionalized quaternary center spirooxindole scaffold in a high chemical yield. A study using the Molecular Electron Density Theory (MEDT) explains the co

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33

Souchet, Michel, J. Guilhem, and François Le Goffic. "A new and easy synthesis of 2-carboxy-6-oxo-cis-octahydroindole." Tetrahedron Letters 28, no. 21 (1987): 2371–74. http://dx.doi.org/10.1016/s0040-4039(00)96127-6.

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34

Vostrikov, Sergey V., Maria E. Konnova, Vladimir V. Turovtzev, Karsten Müller, and Sergey P. Verevkin. "Thermodynamics of hydrogen storage: Equilibrium study of the LOHC system indole/octahydroindole." Fuel 335 (March 2023): 127025. http://dx.doi.org/10.1016/j.fuel.2022.127025.

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35

Kubyshkin, Vladimir, and Nediljko Budisa. "Exploring hydrophobicity limits of polyproline helix with oligomeric octahydroindole-2-carboxylic acid." Journal of Peptide Science 24, no. 4-5 (2018): e3076. http://dx.doi.org/10.1002/psc.3076.

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36

Reilly, Laurence W., Randall B. Nelson,, and Gordon W. Gribble. "Short Synthesis of 2-oxo-1,2,3,4,6,7,12,12b-Octahydroindolo[2,3-a]quinolizine." Organic Preparations and Procedures International 50, no. 5 (2018): 509–11. http://dx.doi.org/10.1080/00304948.2018.1525985.

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37

YAMANAKA, ETSUJI, MAYUMI NARUSHIMA, KUNIE(nee NAGASHIMA) INUKAI, and SHIN-ICHIRO SAKAI. "A convenient synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 1 (1986): 77–81. http://dx.doi.org/10.1248/cpb.34.77.

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38

Solé, Daniel, Joan Bosch, and Josep Bonjoch. "3a-(o-Nitrophenyl)octahydroindol-4-ones: Synthesis and spectroscopic analysis." Tetrahedron 52, no. 11 (1996): 4013–28. http://dx.doi.org/10.1016/s0040-4020(96)00065-8.

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39

Bonjoch, Josep, Juanlo Catena, Esther Isábal, Meritxell López-Canet та Nativitat Valls. "Synthesis of the octahydroindole core of aeruginosins: a new bicyclic α-amino acid". Tetrahedron: Asymmetry 7, № 7 (1996): 1899–902. http://dx.doi.org/10.1016/0957-4166(96)00225-x.

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40

Torras, Juan, Javier G. Warren, Guillem Revilla-López, Ana I. Jiménez, Carlos Cativiela, and Carlos Alemán. "Solvent-induced conformational flexibility of a bicyclic proline analogue: Octahydroindole-2-carboxylic acid." Biopolymers 102, no. 2 (2014): 176–90. http://dx.doi.org/10.1002/bip.22465.

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41

Sayago, Francisco J., Pedro Laborda, M. Isabel Calaza, Ana I. Jiménez, and Carlos Cativiela. "Access to the cis-Fused Stereoisomers of Proline Analogues Containing an Octahydroindole Core." European Journal of Organic Chemistry 2011, no. 11 (2011): 2011–28. http://dx.doi.org/10.1002/ejoc.201001710.

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42

Akhrem, A. A., and Y. G. Chernov. "A New Synthesis of 2,4-Dioxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine." Synthesis 1985, no. 04 (1985): 411–12. http://dx.doi.org/10.1055/s-1985-31222.

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43

Sun, Suya, Youzhi Jia, Ning Zeng, and Famei Li. "Chiral Ligand-Exchange Chromatography for Separation of Three Stereoisomers of Octahydroindole-2-carboxylic Acid." Chromatographia 63, no. 7-8 (2006): 331–35. http://dx.doi.org/10.1365/s10337-006-0752-7.

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44

Sayago, Francisco J., M. Isabel Calaza, Ana I. Jiménez та Carlos Cativiela. "Towards the stereoselective synthesis of α-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid". Tetrahedron: Asymmetry 19, № 24 (2008): 2763–66. http://dx.doi.org/10.1016/j.tetasy.2008.11.030.

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45

Bachmann, Philipp, Matthias Schwarz, Johann Steinhauer, et al. "Dehydrogenation of the Liquid Organic Hydrogen Carrier System Indole/Indoline/Octahydroindole on Pt(111)." Journal of Physical Chemistry C 122, no. 8 (2018): 4470–79. http://dx.doi.org/10.1021/acs.jpcc.7b12625.

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46

Steinhauer, J., P. Bachmann, E. M. Freiberger, U. Bauer, H. P. Steinrück, and C. Papp. "Model Catalytic Studies of Liquid Organic Hydrogen Carriers: Indole/Indoline/Octahydroindole on Ni(111)." Journal of Physical Chemistry C 124, no. 41 (2020): 22559–67. http://dx.doi.org/10.1021/acs.jpcc.0c06988.

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47

Viveros-Ceballos, José Luis, Erick Iván Martínez-Toto, César Eustaquio-Armenta, Carlos Cativiela, and Mario Ordóñez. "First and Highly Stereoselective Synthesis of Both Enantiomers of Octahydroindole-2-phosphonic Acid (OicP)." European Journal of Organic Chemistry 2017, no. 45 (2017): 6781–87. http://dx.doi.org/10.1002/ejoc.201701330.

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48

Lounasmaa, Mauri, Reija Jokela, and Tarja TAmminen. "Conformational Studies of 1- and 3-Ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizines." HETEROCYCLES 23, no. 6 (1985): 1367. http://dx.doi.org/10.3987/r-1985-06-1367.

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49

Badenock, Jeanese C., and Gordon W. Gribble. "The Synthesis of (±)-1,2,3,4,6,7,12,12b-Octahydroindolo[2,3-a]quinolizine from Tryptophan and Dihydropyran." Organic Preparations and Procedures International 50, no. 4 (2018): 449–53. http://dx.doi.org/10.1080/00304948.2018.1468988.

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50

Corts, G. J. B., та W. Th Nauta. "Tetracyclic γ-carboline derivatives: Synthesis of 2,8-substituted octahydroindolo[3,2-α]quinolizines". Recueil des Travaux Chimiques des Pays-Bas 85, № 7 (2010): 744–52. http://dx.doi.org/10.1002/recl.19660850711.

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