Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

A facile method for the solution and solid-phase synthesis of substituted [3.3.1] bicycles.

K C Nicolaou1, J A Pfefferkorn, G Q Cao

  • 1Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu

Organic Letters
|May 24, 2000
PubMed
Summary

Researchers developed an improved selenium-mediated cyclization method for alkenyl-substituted beta-dicarbonyls. This technique efficiently synthesizes bicyclo[3.3.1]nonan-9-ones, valuable in natural product synthesis.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Tales of total synthesis.

Nature reviews. Chemistry·2026
Same author

[Research on the framework of biosafety standards for pathogenic microbial laboratories].

Zhonghua liu xing bing xue za zhi = Zhonghua liuxingbingxue zazhi·2024
Same author

A unified strategy for the total syntheses of eribulin and a macrolactam analogue of halichondrin B.

Proceedings of the National Academy of Sciences of the United States of America·2022
Same author

Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations.

Journal of the American Chemical Society·2022
Same author

A Highly Convergent Total Synthesis of Norhalichondrin B.

Journal of the American Chemical Society·2021
Same author

Corrigendum: The Role of Organic Synthesis in the Emergence and Development of Antibody-Drug Conjugates as Targeted Cancer Therapies.

Angewandte Chemie (International ed. in English)·2021

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Bicyclic natural products, particularly those from the Guttiferae family, are of significant interest due to their complex structures and potential bioactivities.
  • Efficient synthetic routes are crucial for accessing these valuable compounds and their analogs for further study.
  • Selenium-mediated cyclizations offer a powerful strategy for forming carbon-carbon bonds and constructing cyclic systems.

Purpose of the Study:

  • To develop an improved method for the synthesis of bicyclo[3.3.1]nonan-9-ones.
  • To explore the application of selenium-mediated cyclization for constructing these bicyclic frameworks.
  • To demonstrate the versatility of the method in both solution-phase and solid-phase synthesis.

Main Methods:

Related Experiment Videos

  • Utilized alkenyl-substituted beta-dicarbonyls as starting materials.
  • Employed selenium-mediated cyclization as the key synthetic transformation.
  • Performed reactions in both solution and on solid support for comparative analysis.

Main Results:

  • Successfully synthesized a variety of bicyclo[3.3.1]nonan-9-ones.
  • The improved selenium-mediated cyclization proved efficient and versatile.
  • Demonstrated applicability for both solution and solid-phase synthetic strategies.

Conclusions:

  • The developed selenium-mediated cyclization is an effective method for accessing bicyclo[3.3.1]nonan-9-ones.
  • This approach facilitates the synthesis of important bicyclic scaffolds found in natural products.
  • The method's compatibility with solid-phase synthesis broadens its utility in combinatorial chemistry and drug discovery.