Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

Scholarly Works

• Parte, L. G.; Fernández, S.; Sandonís, E.; Guerra, J.; López, E. Transition-Metal-Catalyzed Transformations for the Synthesis of Marine Drugs. Marine drugs 2024, 22, 253. doi:10.3390/md22060253
• Reissig, H.-U.; Alam Chowdhury, M. Asymmetric Synthesis of the Unnatural Enantiomer of Codonopsinine and a Stereoisomer via Alkoxyallenes. HETEROCYCLES 2023, 106, 858. doi:10.3987/com-23-14837
• Harris, R. J.; Nakafuku, K.; Duncan, A. N.; Carden, R. G.; Timmerman, J. C.; Widenhoefer, R. A. Kinetics and Mechanism of the Gold-Catalyzed Hydroamination of 1,1-Dimethylallene with N-Methylaniline. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 10377–10386. doi:10.1002/chem.202100741
• Reissig, V. M. S. a. H.-U. Alkoxyallenes as Starting Materials for the Syntheses of Natural Products. Current Organic Chemistry 2020, 23, 2976–3003. doi:10.2174/1385272824666191218115731
• Harris, R. J.; Carden, R. G.; Duncan, A. N.; Widenhoefer, R. A. Kinetics and Mechanism of the Gold-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols. ACS Catalysis 2018, 8, 8941–8952. doi:10.1021/acscatal.8b02211
• Amombo, G. M. O.; Flögel, O.; Kalai, S. K. D.; Schoder, S.; Warzok, U.; Reissig, H.-U. Efficient Syntheses of 2,5‐Dihydropyrroles, Pyrrolidin‐3‐ones, and Electron‐Rich Pyrroles from N‐Tosylimines and Lithiated Alkoxyallenes. European Journal of Organic Chemistry 2017, 2017, 1965–1972. doi:10.1002/ejoc.201700073
• Pflästerer, D.; Hashmi, A. S. K. Gold catalysis in total synthesis – recent achievements. Chemical Society reviews 2016, 45, 1331–1367. doi:10.1039/c5cs00721f
• Mezeiová, E.; Martinková, M.; Stanková, K.; Fabišíková, M.; Gonda, J.; Pilátová, M.; Gönciová, G. Total synthesis and antiproliferative/cytotoxic profiling of 2-epi-jaspine B. Carbohydrate research 2016, 423, 70–81. doi:10.1016/j.carres.2016.01.011
• Martinková, M.; Gonda, J. Marine cytotoxic jaspine B and its stereoisomers: biological activity and syntheses. Carbohydrate research 2016, 423, 1–42. doi:10.1016/j.carres.2016.01.009
• Fujiwara, T.; Liu, B.; Niu, W.; Hashimoto, K.; Nambu, H.; Yakura, T. Practical Synthesis of Pachastrissamine (Jaspine B), 2-epi-Pachastrissamine, and the 2-epi-Pyrrolidine Analogue. Chemical & pharmaceutical bulletin 2016, 64, 179–188. doi:10.1248/cpb.c15-00816
• Liu, B.; Hashimoto, K.; Nambu, H.; Fujiwara, T.; Yakura, T. Synthetic Studies on a Pachastrissamine Sulfur Analogue: Synthesis of a 4-epi-Sulfur Analogue. Chemical & pharmaceutical bulletin 2016, 64, 366–370. doi:10.1248/cpb.c15-00996
• Kwon, Y.; Song, J.; Bae, H.; Kim, W.-J.; Lee, J.-Y.; Han, G.-H.; Lee, S. K.; Kim, S. Synthesis and Biological Evaluation of Carbocyclic Analogues of Pachastrissamine. Marine drugs 2015, 13, 824–837. doi:10.3390/md13020824
• Martinková, M.; Mezeiová, E.; Fabišíková, M.; Gonda, J.; Pilátová, M.; Mojžiš, J. Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation. Carbohydrate research 2014, 402, 6–24. doi:10.1016/j.carres.2014.11.004
• Martinková, M.; Mezeiová, E.; Gonda, J.; Jacková, D.; Pomikalová, K. Total synthesis of (−)-jaspine B and its 4-epi-analogue from d-xylose. Tetrahedron: Asymmetry 2014, 25, 750–766. doi:10.1016/j.tetasy.2014.04.002
• Zimmer, R.; Reissig, H.-U. Alkoxyallenes as building blocks for organic synthesis. Chemical Society reviews 2014, 43, 2888–2903. doi:10.1039/c3cs60429b

Explore citations to this article at