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
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
ISSN: 1099-0690
Date of registration: 3-Mar-2021
Description of the related object: Supporting Information
Related object:
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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