Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Dec 22;6(1):881-888.
doi: 10.1021/acsomega.0c05484. eCollection 2021 Jan 12.

Total Synthesis of Marine Alkaloids Motuporamines A and B via Ring Expansion of Cyclic β-Keto Esters

Zi-Jie Song  1 , Shu-Yu Meng  1 , Quan-Rui Wang  1
Affiliations

Total Synthesis of Marine Alkaloids Motuporamines A and B via Ring Expansion of Cyclic β-Keto Esters

Zi-Jie Song et al. ACS Omega. .

Abstract

An expedient total synthesis of the title marine sponge alkaloids has been developed. The salient features of the synthesis are as follows: (i) preparation of the required 13- and 14-membered cyclic lactams with n + 4 ring-expansion strategy of cyclic β-keto esters and (ii) functional group manipulation of the resulted keto ester lactams. This approach used easily accessible and inexpensive materials/reagents, thus providing a promising alternative to the existing preparations.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Structures of motuporamines A (1) and B (2).
Scheme 1
Scheme 1. Synthetic Route to 13-Membered Keto-Lactam 10
Scheme 2
Scheme 2. Synthesis of TFA Salt of Motuporamine A (1·TFA)
Scheme 3
Scheme 3. Synthetic Route to 14-Membered Keto-Lactam 22
Scheme 4
Scheme 4. Synthesis of TFA Salt of Motuporamine B (2·TFA)
See this image and copyright information in PMC

References

    1. Mudit M.; El Sayed K. A. Cancer control potential of marine natural product scaffolds through inhibition of tumor cell migration and invasion. Drug Discovery Today 2016, 21, 1745–1760. 10.1016/j.drudis.2016.06.032. - DOI - PubMed
    1. Althagbi H. I.; Alarif W. M.; Al-Footy K. O.; Abdel-Lateff A. Marine-Derived Macrocyclic Alkaloids (MDMAs): Chemical and Biological Diversity. Mar. Drugs 2020, 18, 36810.3390/md18070368. - DOI - PMC - PubMed
    1. Williams D. E.; Lassota P.; Andersen R. J. Motuporamines A–C, Cytotoxic Alkaloids Isolated from the Marine Sponge Xestospongia exigua (Kirkpatrick). J. Org. Chem. 1998, 63, 4838–4841. 10.1021/jo980355p. - DOI - PubMed
    1. Williams D. E.; Craig K. S.; Patrick B.; McHardy L. M.; van Soest R.; Roberge M.; Andersen R. J. Motuporamines, Anti-Invasion and Anti-Angiogenic Alkaloids from the Marine Sponge Xestospongia exigua (Kirkpatrick): Isolation, Structure Elucidation, Analogue Synthesis, and Conformational Analysis. J. Org. Chem. 2002, 67, 245–258. 10.1021/jo016101c. - DOI - PubMed
    1. Borselli D.; Blanchet M.; Bolla J.-M.; Muth A.; Skruber K.; Phanstiel O.; Brunel J. M. Motuporamine Derivatives as Antimicrobial Agents and Antibiotic Enhancers against Resistant Gram-Negative Bacteria. ChemBioChem 2017, 18, 276–283. 10.1002/cbic.201600532. - DOI - PMC - PubMed