Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

A Hypothesis Concerning the Biosynthesis of the Obtusallene Family of Marine Natural Products via Electrophilic Bromination

View Author Information
Department of Chemistry, Imperial College London, London SW7 2AZ, UK
Cite this: Org. Lett. 2006, 8, 26, 6055–6058
Publication Date (Web):November 30, 2006
https://doi.org/10.1021/ol062520q
Copyright © 2006 American Chemical Society

    Article Views

    1545

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options

    Abstract

    Abstract Image

    A hypothesis concerning the biosynthesis of the marine natural product family the obtusallenes is proposed. Multiple electrophilic bromination events are invoked.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 42 publications.

    1. Harry B. Hicks, Daniel S. Brown, Hau Sun Sam Chan, Bruno A. Sousa, Kirsten E. Christensen, Jonathan W. Burton. Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne. Organic Letters 2022, 24 (50) , 9174-9178. https://doi.org/10.1021/acs.orglett.2c03524
    2. Meera Johny, Rose Mary Philip, Goreti Rajendar. Highly Regio- and Stereoselective Intramolecular Rearrangement of Glycidol Acetal to Alkoxy Cyclic Acetals. Organic Letters 2022, 24 (33) , 6165-6170. https://doi.org/10.1021/acs.orglett.2c02397
    3. Hau Sun Sam Chan, Q. Nhu N. Nguyen, Robert S. Paton, Jonathan W. Burton. Synthesis, Characterization, and Reactivity of Complex Tricyclic Oxonium Ions, Proposed Intermediates in Natural Product Biosynthesis. Journal of the American Chemical Society 2019, 141 (40) , 15951-15962. https://doi.org/10.1021/jacs.9b07438
    4. Yu-An Zhang, Natalie Yaw, Scott A. Snyder. General Synthetic Approach for the Laurencia Family of Natural Products Empowered by a Potentially Biomimetic Ring Expansion. Journal of the American Chemical Society 2019, 141 (19) , 7776-7788. https://doi.org/10.1021/jacs.9b01088
    5. Erin D. Shepherd, Bryony S. Dyson, William E. Hak, Quynh Nhu N. Nguyen, Miseon Lee, Mi Jung Kim, Te-ik Sohn, Deukjoon Kim, Jonathan W. Burton, Robert S. Paton. Structure Determination of a Chloroenyne from Laurencia majuscula Using Computational Methods and Total Synthesis. The Journal of Organic Chemistry 2019, 84 (9) , 4971-4991. https://doi.org/10.1021/acs.joc.8b02975
    6. Stamatios Perdikaris, Alfonso Mangoni, Laura Grauso, Panagiota Papazafiri, Vassilios Roussis, Efstathia Ioannou. Vagiallene, a Rearranged C15 Acetogenin from Laurencia obtusa. Organic Letters 2019, 21 (9) , 3183-3186. https://doi.org/10.1021/acs.orglett.9b00897
    7. Sylvain Sutour, Bruno Therrien, Stephan H. von Reuss, and Félix Tomi . Halogenated C15 Acetogenin Analogues of Obtusallene III from a Laurenciella sp. Collected in Corsica. Journal of Natural Products 2018, 81 (2) , 279-285. https://doi.org/10.1021/acs.jnatprod.7b00706
    8. James Clarke, Karl J. Bonney, Muhammad Yaqoob, Savade Solanki, Henry S. Rzepa, Andrew J. P. White, David S. Millan, and D. Christopher Braddock . Epimeric Face-Selective Oxidations and Diastereodivergent Transannular Oxonium Ion Formation Fragmentations: Computational Modeling and Total Syntheses of 12-Epoxyobtusallene IV, 12-Epoxyobtusallene II, Obtusallene X, Marilzabicycloallene C, and Marilzabicycloallene D. The Journal of Organic Chemistry 2016, 81 (20) , 9539-9552. https://doi.org/10.1021/acs.joc.6b02008
    9. Iljin Shin, Dongjoo Lee, and Hyoungsu Kim . Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (−)-Bisezakyne A. Organic Letters 2016, 18 (17) , 4420-4423. https://doi.org/10.1021/acs.orglett.6b02239
    10. Adrián Gutiérrez-Cepeda, José J. Fernández, Manuel Norte, Matías López-Rodríguez, Iván Brito, Christian D. Muller, and María L. Souto . Additional Insights into the Obtusallene Family: Components of Laurencia marilzae. Journal of Natural Products 2016, 79 (4) , 1184-1188. https://doi.org/10.1021/acs.jnatprod.5b01080
    11. Jing Zhou and Ying-Yeung Yeung . N-Bromosuccinimide-Induced Aminocyclization–Aziridine Ring-Expansion Cascade: An Asymmetric and Highly Stereoselective Approach toward the Synthesis of Azepane. Organic Letters 2014, 16 (8) , 2134-2137. https://doi.org/10.1021/ol5005609
    12. Bin-Gui Wang, James B. Gloer, Nai-Yun Ji, and Jian-Chun Zhao . Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology. Chemical Reviews 2013, 113 (5) , 3632-3685. https://doi.org/10.1021/cr9002215
    13. Karl J. Bonney and D. Christopher Braddock . A Unifying Stereochemical Analysis for the Formation of Halogenated C15-Acetogenin Medium-Ring Ethers From Laurencia Species via Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening and Experimental Corroboration with a Model Epoxide. The Journal of Organic Chemistry 2012, 77 (21) , 9574-9584. https://doi.org/10.1021/jo301580c
    14. Scott A. Snyder, Alexandria P. Brucks, Daniel S. Treitler, and Ioana Moga . Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne. Journal of the American Chemical Society 2012, 134 (42) , 17714-17721. https://doi.org/10.1021/ja3076988
    15. Bryony S. Dyson, Jonathan W. Burton, Te-ik Sohn, Byungsook Kim, Hoon Bae, and Deukjoon Kim . Total Synthesis and Structure Confirmation of Elatenyne: Success of Computational Methods for NMR Prediction with Highly Flexible Diastereomers. Journal of the American Chemical Society 2012, 134 (28) , 11781-11790. https://doi.org/10.1021/ja304554e
    16. Scott A. Snyder, Daniel S. Treitler, Alexandria P. Brucks, and Wesley Sattler . A General Strategy for the Stereocontrolled Preparation of Diverse 8- and 9-Membered Laurencia-Type Bromoethers. Journal of the American Chemical Society 2011, 133 (40) , 15898-15901. https://doi.org/10.1021/ja2069449
    17. Adrián Gutiérrez-Cepeda, José J. Fernández, Manuel Norte, and María L. Souto . New Bicyclotridecane C15 Nonterpenoid Bromoallenes from Laurencia marilzae. Organic Letters 2011, 13 (10) , 2690-2693. https://doi.org/10.1021/ol200792v
    18. Adrián Gutiérrez-Cepeda, José J. Fernández, Laura V. Gil, Matías López-Rodríguez, Manuel Norte, and María L. Souto . Nonterpenoid C15 Acetogenins from Laurencia marilzae. Journal of Natural Products 2011, 74 (3) , 441-448. https://doi.org/10.1021/np100866g
    19. D. Christopher Braddock, David S. Millan, Yolanda Pérez-Fuertes, Rebecca H. Pouwer, Richard N. Sheppard, Savade Solanki and Andrew J. P. White. Bromonium Ion Induced Transannular Oxonium Ion Formation−Fragmentation in Model Obtusallene Systems and Structural Reassignment of Obtusallenes V−VII. The Journal of Organic Chemistry 2009, 74 (5) , 1835-1841. https://doi.org/10.1021/jo8026577
    20. D. Christopher Braddock and Henry S. Rzepa. Structural Reassignment of Obtusallenes V, VI, and VII by GIAO-Based Density Functional Prediction. Journal of Natural Products 2008, 71 (4) , 728-730. https://doi.org/10.1021/np0705918
    21. Owen Smith, Mihai V. Popescu, Madeleine J. Hindson, Robert S. Paton, Jonathan W. Burton, Martin D. Smith. Control of stereogenic oxygen in a helically chiral oxonium ion. Nature 2023, 615 (7952) , 430-435. https://doi.org/10.1038/s41586-023-05719-z
    22. Gordon W. Gribble. Naturally Occurring Organohalogen Compounds—A Comprehensive Review. 2023, 1-546. https://doi.org/10.1007/978-3-031-26629-4_1
    23. Hau Sun Sam Chan, Amber L. Thompson, Kirsten E. Christensen, Jonathan W. Burton. Forwards and backwards – synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C–F. Chemical Science 2020, 11 (42) , 11592-11600. https://doi.org/10.1039/D0SC04120C
    24. Yang Liu, Lijian Ding, Ziming Zhang, Xiaojun Yan, Shan He. New antifungal tetrahydrofuran derivatives from a marine sponge-associated fungus Aspergillus sp. LS78. Fitoterapia 2020, 146 , 104677. https://doi.org/10.1016/j.fitote.2020.104677
    25. Cooper A. Taylor, Yu-An Zhang, Scott A. Snyder. The enantioselective total synthesis of laurendecumallene B. Chemical Science 2020, 11 (11) , 3036-3041. https://doi.org/10.1039/C9SC06116A
    26. Ranjeet Kumar, Ashish Kumar Tewari. Medicinal properties of marine plants. 2018, 257-282. https://doi.org/10.1016/B978-0-08-102071-5.00011-8
    27. Won‐jin Chung, Christopher D. Vanderwal. Stereoselective Halogenation in Natural Product Synthesis. Angewandte Chemie International Edition 2016, 55 (14) , 4396-4434. https://doi.org/10.1002/anie.201506388
    28. Won‐jin Chung, Christopher D. Vanderwal. Stereoselektive Halogenierungen in der Naturstoffsynthese. Angewandte Chemie 2016, 128 (14) , 4470-4510. https://doi.org/10.1002/ange.201506388
    29. Maria Harizani, Efstathia Ioannou, Vassilios Roussis. The Laurencia Paradox: An Endless Source of Chemodiversity. 2016, 91-252. https://doi.org/10.1007/978-3-319-33172-0_2
    30. Te‐ik Sohn, Deukjoon Kim, Robert S. Paton. Substrate‐Controlled Asymmetric Total Syntheses of Microcladallenes A, B, and C Based on the Proposed Structures. Chemistry – A European Journal 2015, 21 (45) , 15988-15997. https://doi.org/10.1002/chem.201502592
    31. Ryan M. Young, Kathryn M. Schoenrock, Jacqueline L. von Salm, Charles D. Amsler, Bill J. Baker. Structure and Function of Macroalgal Natural Products. 2015, 39-73. https://doi.org/10.1007/978-1-4939-2684-8_2
    32. Adrián Gutiérrez-Cepeda, Antonio Daranas, José Fernández, Manuel Norte, María Souto. Stereochemical Determination of Five-Membered Cyclic Ether Acetogenins Using a Spin-Spin Coupling Constant Approach and DFT Calculations. Marine Drugs 2014, 12 (7) , 4031-4044. https://doi.org/10.3390/md12074031
    33. Jing Zhou, Ying-Yeung Yeung. Diastereoselective synthesis of functionalized pyrrolidines through N-bromosuccinimide-induced aziridine ring expansion cascade of cinnamylaziridine. Org. Biomol. Chem. 2014, 12 (38) , 7482-7485. https://doi.org/10.1039/C4OB01384K
    34. Chong Kiat Tan, Yi Zhao, Jing Zhou, Ying‐Yeung Yeung. Stereoselective Halogenations. 2013, 1-20. https://doi.org/10.1002/9781118596784.ssd042
    35. David J. Shepherd, Phillip A. Broadwith, Bryony S. Dyson, Robert S. Paton, Jonathan W. Burton. Structure Reassignment of Laurefurenynes A and B by Computation and Total Synthesis. Chemistry – A European Journal 2013, 19 (38) , 12644-12648. https://doi.org/10.1002/chem.201302349
    36. D. Christopher Braddock, James Clarke, Henry S. Rzepa. Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide – Favorskii manifold. Chemical Communications 2013, 49 (95) , 11176. https://doi.org/10.1039/c3cc46720a
    37. Francisco Cen Pacheco, Janny A. Villa-Pulgarin, Faustino Mollinedo, Manuel Norte Martín, José Javier Fernández, Antonio Hernández Daranas. New Polyether Triterpenoids from Laurencia viridis and Their Biological Evaluation. Marine Drugs 2011, 9 (11) , 2220-2235. https://doi.org/10.3390/md9112220
    38. Davide Vione, Valter Maurino, Simona Cucu Man, Swapan Khanra, Cecilia Arsene, Romeo‐Iulian Olariu, Claudio Minero. Formation of Organobrominated Compounds in the Presence of Bromide under Simulated Atmospheric Aerosol Conditions. ChemSusChem 2008, 1 (3) , 197-204. https://doi.org/10.1002/cssc.200700031
    39. Igor Larrosa, Pedro Romea, Fèlix Urpí. Synthesis of six-membered oxygenated heterocycles through carbon–oxygen bond-forming reactions. Tetrahedron 2008, 64 (12) , 2683-2723. https://doi.org/10.1016/j.tet.2007.11.092
    40. D. Christopher Braddock, Roshni Bhuva, Yolanda Pérez-Fuertes, Rebecca Pouwer, Craig A. Roberts, Andrea Ruggiero, Elaine S. E. Stokes, Andrew J. P. White. The stereochemical course of bromoetherification of enynes. Chemical Communications 2008, 30 (12) , 1419. https://doi.org/10.1039/b800054a
    41. Peter H. Buist. Exotic biomodification of fatty acids. Natural Product Reports 2007, 24 (5) , 1110. https://doi.org/10.1039/b508584p
    42. Robert A. Hill. Marine natural products. Annual Reports Section "B" (Organic Chemistry) 2007, 103 , 125. https://doi.org/10.1039/b614408j