Journal article

Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B

Abstract:: A short route from dihydrocarvone is described, which led to the tetracarbocyclic core common to artatrovirenol A and B and daphnenoid A. A variant of this route afforded guaia-4,6-dien-3-one (from Enterospermum madagascarensis) and its epimer. From 2-(2-oxoethyl)furan, a 15-step sequence then delivered the complete carbon skeleton and all functionality necessary for daphnenoid A. Key steps in the route include diastereoselective intramolecular oxidopyrylium cycloaddition, oxa-bridge cleavage under “push–pull” conditions, and intramolecular Diels–Alder cycloaddition.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Zong, J., Christensen, K. E., & Robertson, J. (2024). Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B. Organic Letters, 26(8), 1556–1560.

MLA Style

Zong, J., et al. “Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B.” Organic Letters, vol. 26, no. 8, American Chemical Society, 2024, pp. 1556–60.

Chicago Style

Zong, J, KE Christensen, and J Robertson. 2024. “Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B.” Organic Letters 26 (8): 1556–60.
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Files:: Zong_et_al_2024_Routes_to_Advanced.pdf

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Publisher copy:: 10.1021/acs.orglett.3c04199

Authors

+ Zong, J More by this author

Institution:: University of Oxford
Division:: HUMS
Department:: Classics Faculty
Sub department:: Chemistry Research Laboratory
Role:: Author
ORCID:: 0009-0006-9968-5522

+ Christensen, KE More by this author

Institution:: University of Oxford
Division:: HUMS
Department:: Classics Faculty
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Robertson, J More by this author

Institution:: University of Oxford
Division:: HUMS
Department:: Classics Faculty
Sub department:: Chemistry Research Laboratory
Role:: Author
ORCID:: 0000-0002-6809-8265

Publisher:: American Chemical Society
Journal:: Organic Letters More from this journal
Volume:: 26
Issue:: 8
Pages:: 1556-1560
Publication date:: 2024-02-19
Acceptance date:: 2024-02-14
DOI:: 10.1021/acs.orglett.3c04199
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Source identifiers:: 1801566
Deposit date:: 2024-05-30

Terms of use

Copyright date:: 2024

Licence:: CC Attribution (CC BY)

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