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Open AccessArticle

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 Natural Products Total Synthesis)
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
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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.

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