Next Article in Journal
Tri-Herbal Medicine Divya Sarva-Kalp-Kwath (Livogrit) Regulates Fatty Acid-Induced Steatosis in Human HepG2 Cells through Inhibition of Intracellular Triglycerides and Extracellular Glycerol Levels
Next Article in Special Issue
Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine
Previous Article in Journal
Structural Evolution and Magnetic Properties of Gd2Hf2O7 Nanocrystals: Computational and Experimental Investigations
Article

Total Synthesis of Phorbazole B

1
Department of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, Norway
2
Department of Chemistry and Centre for Pharmacy, University of Bergen, Allégaten 41, 5007 Bergen, Norway
*
Authors to whom correspondence should be addressed.
Academic Editors: Magne Olav Sydnes and Joanne Harvey
Molecules 2020, 25(20), 4848; https://doi.org/10.3390/molecules25204848
Received: 19 September 2020 / Revised: 14 October 2020 / Accepted: 18 October 2020 / Published: 21 October 2020
(This article belongs to the Special Issue Total Synthesis of Natural Products)
Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC. View Full-Text
Keywords: phorbazole; oxazole; pyrrole; late-stage chlorination phorbazole; oxazole; pyrrole; late-stage chlorination
Show Figures

Graphical abstract

MDPI and ACS Style

Guttormsen, Y.; Fairhurst, M.E.; Pandey, S.K.; Isaksson, J.; Haug, B.E.; Bayer, A. Total Synthesis of Phorbazole B. Molecules 2020, 25, 4848. https://doi.org/10.3390/molecules25204848

AMA Style

Guttormsen Y, Fairhurst ME, Pandey SK, Isaksson J, Haug BE, Bayer A. Total Synthesis of Phorbazole B. Molecules. 2020; 25(20):4848. https://doi.org/10.3390/molecules25204848

Chicago/Turabian Style

Guttormsen, Yngve, Magnus E. Fairhurst, Sunil K. Pandey, Johan Isaksson, Bengt E. Haug, and Annette Bayer. 2020. "Total Synthesis of Phorbazole B" Molecules 25, no. 20: 4848. https://doi.org/10.3390/molecules25204848

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop