IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-32902-z.html
   My bibliography  Save this article

Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core

Author

Listed:
  • Sangbin Park

    (Korea Advanced Institute of Science & Technology (KAIST))

  • Gyumin Kang

    (Korea Advanced Institute of Science & Technology (KAIST)
    Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS))

  • Chansu Kim

    (Korea Advanced Institute of Science & Technology (KAIST))

  • Dongwook Kim

    (Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS))

  • Sunkyu Han

    (Korea Advanced Institute of Science & Technology (KAIST)
    Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS))

Abstract

Securinega alkaloids have fascinated the synthetic chemical community for over six decades. Historically, major research foci in securinega alkaloid synthesis have been on the efficient construction of the fused tetracyclic framework that bears a butenolide moiety and tertiary amine-based heterocycles. These “basic” securinega alkaloids have evolved to undergo biosynthetic oxidative diversifications, especially on the piperidine core. However, a general synthetic solution to access these high-oxidation state securinega alkaloids is lacking. In this study, we have completed the total synthesis of various C4-oxygenated securinine-type alkaloids including securingines A, C, D, securitinine, secu’amamine D, phyllanthine, and 4-epi-phyllanthine. Our synthetic strategy features stereocontrolled oxidation, rearrangement, and epimerization at N1 and C2–C4 positions of the piperidine core within (neo)securinane scaffolds. Our discoveries provide a fundamental synthetic solution to all known securinine-type natural products with various oxidative and stereochemical variations around the central piperidine ring.

Suggested Citation

  • Sangbin Park & Gyumin Kang & Chansu Kim & Dongwook Kim & Sunkyu Han, 2022. "Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32902-z
    DOI: 10.1038/s41467-022-32902-z
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-32902-z
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-32902-z?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    1. Yu Zhao & Jason Rodrigo & Amir H. Hoveyda & Marc L. Snapper, 2006. "Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule," Nature, Nature, vol. 443(7107), pages 67-70, September.
    2. Yong Wang & Hayden M. Carder & Alison E. Wendlandt, 2020. "Synthesis of rare sugar isomers through site-selective epimerization," Nature, Nature, vol. 578(7795), pages 403-408, February.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Małgorzata Staszczyk & Anna Jurczak & Marcin Magacz & Dorota Kościelniak & Iwona Gregorczyk-Maga & Małgorzata Jamka-Kasprzyk & Magdalena Kępisty & Iwona Kołodziej & Magdalena Kukurba-Setkowicz & Wirgi, 2020. "Effect of Polyols and Selected Dental Materials on the Ability to Create a Cariogenic Biofilm–On Children Caries-Associated Streptococcus Mutans Isolates," IJERPH, MDPI, vol. 17(10), pages 1-20, May.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32902-z. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.