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  Catalytic Asymmetric Spirocyclizing Diels–Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of α-Chamigrene, β-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid

Ghosh, S., Erchinger, J. E., Maji, R., & List, B. (2022). Catalytic Asymmetric Spirocyclizing Diels–Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of α-Chamigrene, β-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid. Journal of the American Chemical Society, 144(15), 6703-6708. doi:10.1021/jacs.2c01971.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000A-82DE-9 Version Permalink: https://hdl.handle.net/21.11116/0000-000A-A15D-8
Genre: Journal Article

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Ghosh-Erchinger-Maji-List.pdf (Publisher version), 4MB
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 Creators:
Ghosh, Santanu1, Author           
Erchinger, Johannes Eike1, Author           
Maji, Rajat1, Author           
List, Benjamin1, Author           
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 Abstract: We disclose a general catalytic enantioselective Diels–Alder reaction of exo-enones with dienes to give spirocyclanes. The obtained products feature highly congested quaternary stereogenic spirocenters and are used in concise total and formal syntheses of several sesquiterpenes, including of α-chamigrene, β-chamigrene, laurencenone C, colletoic acid, and omphalic acid. The stereo- and regioselectivities of our spirocyclizing cycloaddition are effectively controlled by strongly acidic and confined imidodiphosphorimidate catalysts. Computational studies shed light on the origin of reactivity and selectivity.

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Language(s): eng - English
 Dates: 2022-02-202022-04-072022-04-20
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.2c01971
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 144 (15) Sequence Number: - Start / End Page: 6703 - 6708 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870