Total Syntheses of Dysidealactams E and F and Dysidealactone B, Drimane-Type Sesquiterpenes Derived from a Dysidea sp. of Marine Sponge

Chen, Yuhao; Lan, Ping; White, Lorenzo V.; Yang, Weiguang; Banwell, Martin G.

doi:10.1055/a-2002-8680

Cited by 3 publications

(2 citation statements)

References 55 publications

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“…Due to a prolonged storage in EtOH, it is quite common to observe the esterifaction of carboxylic acid groups to the corresponding ethyl esters [42]. The dysidealactams and dysidealactones immediately attracted the attention of synthetic chemists, with successful synthesis reported in 2023 [69].…”

Section: Dysidealactamsmentioning

confidence: 99%

Case Studies in Molecular Network-Guided Marine Biodiscovery

2023

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In reviewing a selection of recent case studies from our laboratory, we revealed some lessons learned and benefits accrued from the application of mass spectrometry (MS/MS) molecular networking in the field of marine sponge natural products. Molecular networking proved pivotal to our discovery of many new natural products and even new classes of natural product, some of which were opaque to alternate dereplication and prioritization strategies. Case studies included the discovery of: (i) trachycladindoles, an exceptionally rare class of bioactive indole alkaloid previously only known from a single southern Australia sample of Trachycladus laevispirulifer; (ii) dysidealactams, an unprecedented class of sesquiterpene glycinyl-lactam and glycinyl-imide from a Dysidea sp., a sponge genera often discounted as having been exhaustively studied; (iii) cacolides, an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides from a Cacospongia sp., all too easily mischaracterized and deprioritized during dereplication as a well-known class of sponge sesterterpene tetronic acids; and (iv) thorectandrins, a new class of indole alkaloid which revealed unexpected insights into the chemical and biological properties of the aplysinopsins, one of the earliest and more extensively reported class of sponge natural products.

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Section: Dysidealactamsmentioning

confidence: 99%

Case Studies in Molecular Network-Guided Marine Biodiscovery

2023

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“…27 In addition, Banwell describes the total synthesis of dysidealactams E and F as well as dysidealactone B. 28 Rueping and Yue describe a Ni-catalyzed technique for incorporating selenium atoms at sp 2 sites with aryl iodides as counterparts. 29 Following up on their interest in C–H functionalization, Chen and Zhao report a radical-based approach for accessing isoindolinones with ammonium persulfate as the oxidant.…”

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confidence: 99%

Cluster Preface: Special Issue Honoring Masahiro Murakami’s Contributions to Science

Martı́n¹

2023

Synlett

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Ruben Martin (left) was born in Barcelona in 1976. After receiving his PhD at the Universitat de Barcelona with Prof. Antoni Riera, he moved in January 2004 to the Max-Planck-Institut für Kohlenforschung, Mülheim, as a Humboldt postdoctoral fellow with Prof. Alois Fürstner, where he worked on iron cross-coupling reactions. In May 2005, he undertook further postdoctoral studies at the Massachusetts Institute of Technology with Prof. Stephen L. Buchwald where he developed new metal-catalyzed C–C and C–N bond-forming reactions. In September 2008, he initiated his independent career as an Assistant Professor at ICIQ (Tarragona). In July 2013, he was promoted to Associate Professor and subsequently to ICREA Research Professor. His research interests concern the discovery and development of synthetically useful organometallic methodologies. Masahiro Murakami (right) studied chemistry at the University of Tokyo under the supervision of Professor Mukaiyama, receiving his doctoral degree in science in 1984. He started his career with a research assistant position to Professor Mukaiyama at the same place. In 1987, he moved to Kyoto University to take a research assistant position to the late Professor Yoshihiko Ito (1937–2006). He took a leave from May in 1991 to March in 1992 to work for Professor Albert Eschenmoser at ETH Zürich as a post-doctoral fellow. He then returned to Kyoto, being promoted to Associate Professor in 1993 and Professor in 2002. In March 2022, he retired from Kyoto University. His research interests include the development of synthetically useful, yet mechanistically interesting, organic sections, and the utilization of photo-energy for organic synthesis.

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The marine sponge genus Dysidea sp: the biological and chemical aspects—a review

Fathallah,

Tamer,

Ibrahim

et al. 2023

Futur J Pharm Sci

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Background Marine sponges and other marine invertebrates are considered hidden treasures for a variety of secondary metabolites with pharmacognostic and pharmacological activities which have the potential to create future “super drugs.” The main body of the abstract Dysidea species is one of the most widely distributed sponge species in the world which is found mainly near the shores of the Red Sea, Australia, Yap State, and the Philippines. Dysidea species are considered a source of bioactive natural metabolites that exhibit outstanding chemical diversity. They revealed polybrominated diphenyl ethers, sesquiterpene hydroquinones, furano-sesquiterpenes, diterpenes, chlorinated diketopiperazines, and Amino acids. They showed a broad spectrum of potent biological activities, such as antimicrobial, antimalarial, anti-inflammatory, antitumor, potent cytostatic, antifungal, and antioxidant activities. Conclusion This review presents an overview of the isolated secondary metabolites from Dysidea species, and their recorded biological activities covering the published reports in the last 30 years.

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Total Syntheses of Dysidealactams E and F and Dysidealactone B, Drimane-Type Sesquiterpenes Derived from a Dysidea sp. of Marine Sponge

Cited by 3 publications

References 55 publications

Case Studies in Molecular Network-Guided Marine Biodiscovery

Case Studies in Molecular Network-Guided Marine Biodiscovery

Cluster Preface: Special Issue Honoring Masahiro Murakami’s Contributions to Science

The marine sponge genus Dysidea sp: the biological and chemical aspects—a review

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