Journal article

Collective synthesis of illudalane sesquiterpenes via cascade inverse electron demand (4 + 2) cycloadditions of thiophene s,s-dioxides

Abstract:: Thiophene S,S-dioxides are underutilized tools for the de novo construction of benzene rings in organic synthesis. We report a collective synthesis of nine illudalane sesquiterpenes using bicyclic thiophene S,S-dioxides as generalized precursors to the indane core of the natural products. Exploiting furans as unusual dienophiles in this inverse electron demand Diels–Alder cascade, this concise and convergent approach enables the synthesis of these targets in as little as five steps. Theoretical studies rationalize the reactivity of thiophene S,S-dioxides with both electron-poor and electron-rich dienophiles and reveal reaction pathways involving either nonpolar pericyclic or bifurcating ambimodal cycloadditions. Overall, this work demonstrates the wider potential of thiophene S,S-dioxides as convenient and flexible precursors to polysubstituted arenes.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Park, K. H. K., Frank, N., Duarte, F., & Anderson, E. A. (2022). Collective synthesis of illudalane sesquiterpenes via cascade inverse electron demand (4 + 2) cycloadditions of thiophene s,s-dioxides. Journal of the American Chemical Society, 144(22), 10017–10024.

MLA Style

Park, K. HK, et al. “Collective Synthesis of Illudalane Sesquiterpenes via Cascade Inverse Electron Demand (4 + 2) Cycloadditions of Thiophene s,s-Dioxides.” Journal of the American Chemical Society, vol. 144, no. 22, American Chemical Society, 2022, pp. 10017–24.

Chicago Style

Park, KHK, N Frank, F Duarte, and EA Anderson. 2022. “Collective Synthesis of Illudalane Sesquiterpenes via Cascade Inverse Electron Demand (4 + 2) Cycloadditions of Thiophene s,s-Dioxides.” Journal of the American Chemical Society 144 (22): 10017–24.
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Files:: Park_et_al_2022_Collective_synthesis_of.pdf

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Publisher copy:: 10.1021/jacs.2c03304

Authors

+ Park, KHK More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Frank, N More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author
ORCID:: 0000-0002-8512-6598

+ Duarte, F More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author
ORCID:: 0000-0002-6062-8209

+ Anderson, EA More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Jesus College
Role:: Author
ORCID:: 0000-0002-4149-0494

+ Engineering and Physical Sciences Research Council More from this funder

Funder identifier:: https://ror.org/0439y7842
Grant:: EP/S013172/1; EP/P020267/1

Publisher:: American Chemical Society
Journal:: Journal of the American Chemical Society More from this journal
Volume:: 144
Issue:: 22
Pages:: 10017-10024
Place of publication:: United States
Publication date:: 2022-05-24
DOI:: 10.1021/jacs.2c03304
EISSN:: 1520-5126
ISSN:: 0002-7863
Pmid:: 35609003

Language:: English
Keywords:: sesquiterpenes

thiophenes

electrons

polycyclic sesquiterpenes

cycloaddition reaction
Pubs id:: 1261519
Local pid:: pubs:1261519
Deposit date:: 2024-06-24

Terms of use

Copyright holder:: Park et al.
Copyright date:: 2022
Rights statement:: © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.

Licence:: CC Attribution (CC BY)

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