Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D - Archive ouverte HAL
Article Dans Une Revue European Journal of Organic Chemistry Année : 2020

Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D

Résumé

The aza‐Piancatelli cyclization provides an expedient synthesis of 4‐aminocyclopentenone building blocks that may be converted into aminocyclopentitols, which are heavily represented motifs among natural products. However, its use as a key step in total synthesis was still unprecedented. Here, we disclose our in‐depth investigations regarding this reaction in order to access highly complex structures representing the core of some natural molecules. The applicability of the cyclization was highlighted by the 3‐step total synthesis of bruceolline D. Thus, we anticipate that this work will lay the ground for further applications in total synthesis
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Dates et versions

hal-02990401 , version 1 (19-11-2020)

Identifiants

Citer

Lucile Marin, Guillaume Force, Vincent Gandon, Emmanuelle Schulz, David Lebøeuf. Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D. European Journal of Organic Chemistry, 2020, 2020 (33), pp.5323-5328. ⟨10.1002/ejoc.202000849⟩. ⟨hal-02990401⟩
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