Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1999, 64, 1147-1153
https://doi.org/10.1135/cccc19991147

Three New Alkaloids, Convolutamines F and G, and Convolutamydine E, from the Floridian Marine Bryozoan Amathia convoluta

Yoshiaki Kamanoa,*, Ayano Kotakea, Hirofumi Hashimaa, Ichiro Hayakawaa, Hatsue Hiraidea, Hui-ping Zhanga, Haruhisa Kizub, Kanki Komiyamac, Masahiko Hayashic and George R. Pettitd

a Faculty of Science, Kanagawa University, Hiratsuka 259-1293, Japan
b Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-11, Japan
c Kitasato Institute, Shirogane, Minato-ku, Tokyo 108-8642, Japan
d Cancer Research Institute and Department of Chemistry, Arizona State University, Tempe, AZ 85287-1604, U.S.A.

Crossref Cited-by Linking

  • D. V. Hrishikesh, Annadate Ritesh A., Pansare Sunil V.: Synthesis and Evaluation of N-Diaminophosphoryl Aminothioureas as Bifunctional Catalysts for Vinylogous Aldol Reactions of Isatins and 2(3H)-Furanones. ACS Omega 2023, 8, 3190. <https://doi.org/10.1021/acsomega.2c06637>
  • Kleks Guy, Holland Darren C., Kennedy Emily K., Avery Vicky M., Carroll Anthony R.: Antiplasmodial Alkaloids from the Australian Bryozoan Amathia lamourouxi. J. Nat. Prod. 2020, 83, 3435. <https://doi.org/10.1021/acs.jnatprod.0c00929>
  • Ciavatta Maria Letizia, Lefranc Florence, Vieira Leandro M., Kiss Robert, Carbone Marianna, van Otterlo Willem A. L., Lopanik Nicole B., Waeschenbach Andrea: The Phylum Bryozoa: From Biology to Biomedical Potential. Marine Drugs 2020, 18, 200. <https://doi.org/10.3390/md18040200>
  • Figuerola, Avila: The Phylum Bryozoa as a Promising Source of Anticancer Drugs. Marine Drugs 2019, 17, 477. <https://doi.org/10.3390/md17080477>
  • Tian Xiang Rong, Tang Hai Feng, Tian Xiao Lin, Hu Jia Jun, Huang Li Li, Gustafson Kirk R: Review of bioactive secondary metabolites from marine bryozoans in the progress of new drugs discovery. Future Medicinal Chemistry 2018, 10, 1497. <https://doi.org/10.4155/fmc-2018-0012>
  • Pandey Ganesh, Khamrai Jagadish: Asymmetric Total Synthesis and Structural Elucidation of Unusual Oxindole Alkaloid Leucolusine. Asian J Org Chem 2016, 5, 621. <https://doi.org/10.1002/ajoc.201600101>
  • Khan Faiz Ahmed, Ahmad Saeed, Kodipelli Naveena, Shivange Gururaj, Anindya Roy: Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation. Org. Biomol. Chem. 2014, 12, 3847. <https://doi.org/10.1039/c3ob42537a>
  • Chen Jinsen, Song Chao, Chen Pei, Zhu Jin: An intermolecular C–H functionalization method for the synthesis of 3-hydroxy-2-oxindoles. Org. Biomol. Chem. 2014, 12, 8390. <https://doi.org/10.1039/C4OB01643B>
  • Bisai Vishnumaya, Bisai Alakesh, Singh Vinod K.: Enantioselective organocatalytic aldol reaction using small organic molecules. Tetrahedron 2012, 68, 4541. <https://doi.org/10.1016/j.tet.2012.03.099>
  • Carroll Anthony R., Wild Seanan J., Duffy Sandra, Avery Vicky M.: Kororamide A, a new tribrominated indole alkaloid from the Australian bryozoan Amathia tortuosa. Tetrahedron Letters 2012, 53, 2873. <https://doi.org/10.1016/j.tetlet.2012.03.126>
  • Khan Faiz Ahmed, Ahmad Saeed: Synthesis of Reported and Revised Structures of Amathamide D and Synthesis of Convolutamine F, H and Lutamide A, C. J. Org. Chem. 2012, 77, 2389. <https://doi.org/10.1021/jo3000173>
  • Liu Yun-Lin, Zhou Jian: Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles. Chem. Commun. 2012, 48, 1919. <https://doi.org/10.1039/c2cc17140f>
  • Aikawa Kohsuke, Mimura Shunsuke, Numata Yukinobu, Mikami Koichi: Palladium‐Catalyzed Enantioselective Ene and Aldol Reactions with Isatins, Keto Esters, and Diketones: Reliable Approach to Chiral Tertiary Alcohols. Eur J Org Chem 2011, 2011, 62. <https://doi.org/10.1002/ejoc.201001356>
  • Davis Rohan A., Sykes Melissa, Avery Vicky M., Camp David, Quinn Ronald J.: Convolutamines I and J, antitrypanosomal alkaloids from the bryozoan Amathia tortusa. Bioorganic & Medicinal Chemistry 2011, 19, 6615. <https://doi.org/10.1016/j.bmc.2011.06.006>
  • Chen Wen-Bing, Du Xi-Lin, Cun Lin-Feng, Zhang Xiao-Mei, Yuan Wei-Cheng: Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (−)-donaxaridine and (R)-chimonamidine. Tetrahedron 2010, 66, 1441. <https://doi.org/10.1016/j.tet.2009.12.041>
  • Marqués-López Eugenia, Herrera Raquel P., Christmann Mathias: Asymmetric organocatalysis in total synthesis – a trial by fire. Nat. Prod. Rep. 2010, 27, 1138. <https://doi.org/10.1039/b924964h>
  • Hara Noriyuki, Nakamura Shuichi, Shibata Norio, Toru Takeshi: First Enantioselective Synthesis of (R)‐Convolutamydine B and E with N‐(Heteroarenesulfonyl)prolinamides. Chemistry A European J 2009, 15, 6790. <https://doi.org/10.1002/chem.200900944>
  • Itoh Takahiko, Ishikawa Hayato, Hayashi Yujiro: Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of ent-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B. Org. Lett. 2009, 11, 3854. <https://doi.org/10.1021/ol901432a>
  • Volk R.-B., Girreser U., Al-Refai M., Laatsch H.: Bromoanaindolone, a novel antimicrobial exometabolite from the cyanobacteriumAnabaena constricta. Natural Product Research 2009, 23, 607. <https://doi.org/10.1080/14786410802114068>
  • Malkov Andrei V., Kabeshov Mikhail A., Bella Marco, Kysilka Ondřej, Malyshev Denis A., Pluháčková Kristýna, Kočovský Pavel: Vicinal Amino Alcohols as Organocatalysts in Asymmetric Cross-Aldol Reaction of Ketones:  Application in the Synthesis of Convolutamydine A. Org. Lett. 2007, 9, 5473. <https://doi.org/10.1021/ol7023983>
  • Sharp Jasmine H., Winson Michael K., Porter Joanne S.: Bryozoan metabolites: an ecological perspective. Nat. Prod. Rep. 2007, 24, 659. <https://doi.org/10.1039/b617546e>
  • Cravotto Giancarlo, Giovenzana Giovanni B., Palmisano Giovanni, Penoni Andrea, Pilati Tullio, Sisti Massimo, Stazi Federica: Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis. Tetrahedron: Asymmetry 2006, 17, 3070. <https://doi.org/10.1016/j.tetasy.2006.11.021>
  • Nakamura Tomoaki, Shirokawa Shin-ichi, Hosokawa Seijiro, Nakazaki Atsuo, Kobayashi Susumu: Enantioselective Total Synthesis of Convolutamydines B and E. Org. Lett. 2006, 8, 677. <https://doi.org/10.1021/ol052871p>
  • Kawasaki Tomomi, Higuchi Kazuhiro: Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat. Prod. Rep. 2005, 22, 761. <https://doi.org/10.1039/b502162f>
  • Kawasaki Tomomi, Nagaoka Miyuki, Satoh Tomoko, Okamoto Ayako, Ukon Rie, Ogawa Atsuyo: Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones. Tetrahedron 2004, 60, 3493. <https://doi.org/10.1016/j.tet.2004.02.031>
  • Narkowicz Christian K., Blackman Adrian J., Lacey Ernest, Gill Jennifer H., Heiland Kirstin: Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta. J. Nat. Prod. 2002, 65, 938. <https://doi.org/10.1021/np010574x>
  • Hashima Hirofumi, Hayashi Masahiko, Kamano Yoshiaki, Sato Nobuhiro: Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C. Bioorganic & Medicinal Chemistry 2000, 8, 1757. <https://doi.org/10.1016/S0968-0896(00)00110-3>
  • Kamano Yoshiaki, Kotake Ayano, Hashima Hirofumi, Hayakawa Ichiro, Hiraide Hatsue, Zhang Hui‐ping, Kizu Haruhisa, Komiyama Kanki, Hayashi Masahiko, Pettit George R.: ChemInform Abstract: Three New Alkaloids, Convolutamines F and G, and Convolutamydine E, from the Floridian Marine Bryozoan Amathia convoluta. ChemInform 1999, 30. <https://doi.org/10.1002/chin.199945254>