Total Synthesis of Phorbazole B
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 dev...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/20/4848 |
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doaj-e30bcf011a6a4b5c87e177ed1ecb444b2020-11-25T02:20:22ZengMDPI AGMolecules1420-30492020-10-01254848484810.3390/molecules25204848Total Synthesis of Phorbazole BYngve Guttormsen0Magnus E. Fairhurst1Sunil K. Pandey2Johan Isaksson3Bengt Erik Haug4Annette Bayer5Department of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, NorwayDepartment of Chemistry and Centre for Pharmacy, University of Bergen, Allégaten 41, 5007 Bergen, NorwayDepartment of Chemistry and Centre for Pharmacy, University of Bergen, Allégaten 41, 5007 Bergen, NorwayDepartment of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, NorwayDepartment of Chemistry and Centre for Pharmacy, University of Bergen, Allégaten 41, 5007 Bergen, NorwayDepartment of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, NorwayPhorbazoles 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.https://www.mdpi.com/1420-3049/25/20/4848phorbazoleoxazolepyrrolelate-stage chlorination |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yngve Guttormsen Magnus E. Fairhurst Sunil K. Pandey Johan Isaksson Bengt Erik Haug Annette Bayer |
| spellingShingle |
Yngve Guttormsen Magnus E. Fairhurst Sunil K. Pandey Johan Isaksson Bengt Erik Haug Annette Bayer Total Synthesis of Phorbazole B Molecules phorbazole oxazole pyrrole late-stage chlorination |
| author_facet |
Yngve Guttormsen Magnus E. Fairhurst Sunil K. Pandey Johan Isaksson Bengt Erik Haug Annette Bayer |
| author_sort |
Yngve Guttormsen |
| title |
Total Synthesis of Phorbazole B |
| title_short |
Total Synthesis of Phorbazole B |
| title_full |
Total Synthesis of Phorbazole B |
| title_fullStr |
Total Synthesis of Phorbazole B |
| title_full_unstemmed |
Total Synthesis of Phorbazole B |
| title_sort |
total synthesis of phorbazole b |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2020-10-01 |
| description |
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. |
| topic |
phorbazole oxazole pyrrole late-stage chlorination |
| url |
https://www.mdpi.com/1420-3049/25/20/4848 |
| work_keys_str_mv |
AT yngveguttormsen totalsynthesisofphorbazoleb AT magnusefairhurst totalsynthesisofphorbazoleb AT sunilkpandey totalsynthesisofphorbazoleb AT johanisaksson totalsynthesisofphorbazoleb AT bengterikhaug totalsynthesisofphorbazoleb AT annettebayer totalsynthesisofphorbazoleb |
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