Privileged Biorenewable Secologanin-Based Diversity-Oriented Synthesis for Pseudo-Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks.
alkaloids
diversity-oriented synthesis
renewable resources
secologanin
sustainable chemistry
Journal
ChemSusChem
ISSN: 1864-564X
Titre abrégé: ChemSusChem
Pays: Germany
ID NLM: 101319536
Informations de publication
Date de publication:
06 Dec 2021
06 Dec 2021
Historique:
revised:
11
10
2021
received:
31
08
2021
pubmed:
13
10
2021
medline:
14
1
2022
entrez:
12
10
2021
Statut:
ppublish
Résumé
Bioprivileged molecules hold great promise for supplementing petrochemicals in sustainable organic synthesis of a diverse bioactive products library. Secologanin, a biorenewable monoterpenoid glucoside with unique structural elements, is the key precursor for thousands of natural monoterpenoid alkaloids. Inspired by its inherent highly congested functional groups, a secologanin-based diversity-oriented synthesis (DOS) strategy for novel pseudo-natural alkaloids was developed. All the reactive units of secologanin were involved in these operation simplicity protocols under mild reaction conditions, including the one-step enantioselective transformation of exocyclic C8, C8/C11, and C8/C9/C10 as well as the chemoenzymatic manipulation of endocyclic C2/C6 via the attack by various nucleophiles. A combinatory scenario of the aforementioned reactions further provided diverse polycyclic products with multiple chiral centers. Preliminary activity screening of these newly constructed molecules led to the discovery of antimalarial and highly potent neuroprotective skeletons. The application of green biorenewable secologanin in diversity-oriented pseudo-natural monoterpenoid alkaloid synthesis might encourage the pursuit of valuable bioactive frameworks.
Identifiants
pubmed: 34636473
doi: 10.1002/cssc.202101868
doi:
Substances chimiques
Alkaloids
0
Antimalarials
0
Iridoid Glucosides
0
Secologanin Tryptamine Alkaloids
0
secologanin
19351-63-4
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5320-5327Subventions
Organisme : Key Projects of Natural Science Foundation of Zhejiang Province
ID : LZ21B020001
Organisme : National Natural Science Foundation of China
ID : 21472170
Organisme : National Key R&D Program of China
ID : 2017YFE0102200
Informations de copyright
© 2021 Wiley-VCH GmbH.
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