Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups

Tong Mu, Bingcheng Wei, Dapeng Zhu and Biao Yu ()
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Tong Mu: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Bingcheng Wei: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Dapeng Zhu: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Biao Yu: University of Chinese Academy of Sciences, Chinese Academy of Sciences

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Pentacyclic triterpenoids (PTs) constitute one of the biggest families of natural products, many with higher oxidation state at the D/E rings possess a wide spectrum of biological activties but are poorly accessible. Here we report a site-selective C-H hydroxylation at the D/E rings of PTs paving a way toward these important natural products. We find that Schönecker and Baran’s Cu-mediated aerobic oxidation can be applied and become site-selective on PT skeletons, as being effected unexpectedly by the chirality of the transient pyridine-imino directing groups. To prove the applicability, starting from the most abundant triterpenoid feedstock oleanane, three representative saponins bearing hydroxyl groups at C16 or C22 are expeditiously synthesized, and barringtogenol C which bears hydroxyl groups at C16, C21, and C22 is synthesized via a sequential hydroxylation as the key steps.

Date: 2020
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DOI: 10.1038/s41467-020-18138-9

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