Paeoveitols A–E from Paeonia veitchii

Liang, Wen-Juan; Ma, Yun‐Bao; Geng, Chang‐An; Huang, Xiaoyan; Xu, Hongbo; Zhang, Xuemei; Chen, Ji‐Jun

doi:10.1016/j.fitote.2015.07.015

Cited by 17 publications

(8 citation statements)

References 18 publications

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“…Apart from one double bond, one carbonyl and one glucose moiety, the remaining unsaturation of 1 required it must contain a ring. Inspection of the 1 H- and 13 C-NMR spectra of 1 indicated a monoterpenoid glycoside with a structure similar to that of paeoveitol B [17]. The 7.8 Hz coupling constant for the anomeric proton H-1′ of the glucose at δ H 4.46 confirmed its axial orientation.…”

Section: Resultsmentioning

confidence: 96%

Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii

Feng

Zheng

et al. 2016

Molecules

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Four new monoterpenoid glycosides 1-4, named magnoliaterpenoid A-D, were isolated from a 50% aqueous acetone extract of flower buds of Magnolia biondii, along with one known compound, (1'R,3'S,5'R,8'S,2Z,4E)-dihydrophaseic acid 3-O-β-d-glucopyranoside (5). Their structures and relative configuration were identified by extensive spectroscopic analysis (IR, UV, MS, 1D and 2D NMR). The aglycones of these four new compounds possess seven-membered rings systems, which are very rare. A plausible biosynthetic route for the four new compounds was proposed via the biogenetic isoprene rule. Compounds 1, 2, 3, and 4 showed no antimicrobial activity at the concentration range of 1.95-250 µg/mL.

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Section: Resultsmentioning

confidence: 96%

Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii

Feng

Zheng

et al. 2016

Molecules

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“…Based on this realization, the biogenesis precursor of paeoveitol may not be the paeoniflorin. Recently, Chen and co-workers have isolated five monoterpene paeoveitols A–E from the same genus plant (Figure ). Inspired by the finding that the benzofuran moiety of paeoveitol is paeoveitol D, which was isolated from the same species, we deduced that paeoveitol D would be one of the precursors of paeoveitol.…”

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confidence: 99%

Biomimetic Total Synthesis of Paeoveitol

Zhang

Guo

et al. 2016

Org. Lett.

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“…Paeoveitol is one of the main antipsychotic components of Radix Paeoniae Rubra. [30][31] In 2017, Chen Jijun's group reported for the first time the enantioselective 6-step total synthesis of Paeoveitol with an overall yield of 42% [32], and the best result was the 7-step total synthesis published by Xie Zhixiang's group with an overall yield of 26% [33]. SPA catalyzed hetero Diels alter reaction, as a key step, provides high yield (up to 95%) and good corresponding selectivity (up to 90% ee).…”

Section: Introductionmentioning

confidence: 99%

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

Yang

2021

E3S Web Conf.

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With a 10 years development, chiral spirocyclic phosphoric acids (SPAs) have attracted a substantial amount of attention from the synthetic organic chemistry community. This kind of small molecule organic catalysts has some advantages like easy to obtain, no transition metal and wide application range. Because of avoiding the use of toxic substances which are limited in the process of drug synthesis, a large number of studies pay attention to the key structures (such as indole, carbozole.) containing pharmacological active components in natural products. And most of them get a excellent result in yields (more than 80% yield) and enantioselectivities (more than 90% ee). These studies can provide new pathways to nature products.

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Paeoveitols A–E from Paeonia veitchii

Cited by 17 publications

References 18 publications

Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii

Four New Monoterpenoid Glycosides from the Flower Buds of Magnolia biondii

Biomimetic Total Synthesis of Paeoveitol

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

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