4.8 Article

Privileged Biorenewable Secologanin-Based Diversity-Oriented Synthesis for Pseudo-Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks

期刊

CHEMSUSCHEM
卷 14, 期 23, 页码 5320-5327

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202101868

关键词

alkaloids; diversity-oriented synthesis; renewable resources; secologanin; sustainable chemistry

资金

  1. Key Projects of Natural Science Foundation of Zhejiang Province [LZ21B020001]
  2. National Natural Science Foundation of China [21472170]
  3. National Key R&D Program of China [2017YFE0102200]

向作者/读者索取更多资源

Utilizing secologanin as a starting material, a diversity-oriented synthesis approach was developed to successfully synthesize novel pseudo-natural alkaloids, laying the foundation for producing polycyclic products with multiple chiral centers. These newly constructed molecules showed antimalarial and highly potent neuroprotective properties after preliminary activity screening.
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.

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