Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core - Chimie Théorique et Modèles (iSm2) Accéder directement au contenu
Article Dans Une Revue Chemical Science Année : 2024

Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core

Résumé

Enantioselective construction of small molecules displaying a configurationally stable helical shape built on a fused-tetracyclic core is a daunting synthetic challenge even more pronounced when five-membered rings are incorporated in the structure. The resulting higher configurational lability strongly hampers their access, and therefore the development of new efficient methodologies is timely and highly desirable. In this context, we describe a padlocking approach via the enantioselective organocatalytic domino furannulation of appropriately designed achiral fused-tricyclic precursors resulting in the synthesis of configurationally locked helically chiral tetracyclic scaffolds featuring one or two five-membered rings with the simultaneous control of central and helical chiralities.
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Dates et versions

hal-04616826 , version 1 (19-06-2024)

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Arthur Gaucherand, Expédite Yen-Pon, Diego García-López, Jean-Valère Naubron, Sara Chentouf, et al.. Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core. Chemical Science, 2024, 15 (19), pp.7300 - 7307. ⟨10.1039/d4sc00745j⟩. ⟨hal-04616826⟩

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