Please use this identifier to cite or link to this item:
doi:10.22028/D291-33495
Title: | Atroposelective Synthesis of Isoriccardin C through a C−H Activated Heck Type Macrocyclization |
Author(s): | Marx, Lisa Lamberty, Daniel Choppin, Sabine Colobert, Françoise Speicher, Andreas |
Language: | English |
Title: | European Journal of Organic Chemistry |
Volume: | 2021 |
Issue: | 9 |
Pages: | 1351-1354 |
Publisher/Platform: | Wiley |
Year of Publication: | 2021 |
Free key words: | Atropisomerism Biaryls C−H activation Directing group Natural cyclophanes |
DDC notations: | 500 Science |
Publikation type: | Journal Article |
Abstract: | Macrocyclization is typically the key step in syntheses of cyclophane‐type natural products. Considering compounds with axially chiral biaryl moieties, the control of atroposelectivity is essential for biological activity and is synthetically challenging. Herein we report on atroposelective macrocyclization involving an oxidative Heck type process and enabling the first atropo‐enantiopure synthesis of isoriccardin C. A chiral sulfinyl auxiliary in the ortho‐position of a biaryl axis (still flexible) was used to induce a C−H activated atropodiastereoselective oxidative Heck coupling (>98 % de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target molecule with >98 % ee as well. |
DOI of the first publication: | 10.1002/ejoc.202100017 |
Link to this record: | urn:nbn:de:bsz:291--ds-334957 hdl:20.500.11880/30786 http://dx.doi.org/10.22028/D291-33495 |
ISSN: | 1099-0690 1434-193X |
Date of registration: | 3-Mar-2021 |
Description of the related object: | Supporting Information |
Related object: | https://chemistry-europe.onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fejoc.202100017&file=ejoc202100017-sup-0001-misc_information.pdf |
Faculty: | NT - Naturwissenschaftlich- Technische Fakultät |
Department: | NT - Chemie |
Professorship: | NT - Keiner Professur zugeordnet |
Collections: | SciDok - Der Wissenschaftsserver der Universität des Saarlandes |
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File | Description | Size | Format | |
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ejoc.202100017.pdf | 4,48 MB | Adobe PDF | View/Open |
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