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

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.

journal_name

Nat Commun

journal_title

Nature communications

authors

Mu T,Wei B,Zhu D,Yu B

doi

10.1038/s41467-020-18138-9

subject

Has Abstract

pub_date

2020-09-01 00:00:00

pages

4371

issue

1

issn

2041-1723

pii

10.1038/s41467-020-18138-9

journal_volume

11

pub_type

杂志文章

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