Isolation and Asymmetric Total Synthesis of Perforanoid A

Lv, Chao; Yan, Xiaohui; Tu, Qian; Di, Ying‐Tong; Yuan, Chun‐Mao; Fang, Xin; Ben-David, Yaacove; Xia, Lei; Gong, Jianxian; Shen, Yingbin; Yang, Zhen; Hao, Xiao‐Jiang

doi:10.1002/anie.201602783

Cited by 65 publications

(19 citation statements)

References 68 publications

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“…Previous investigations of the chemical constituents of this plant have revealed an array of structurally diverse chromones, quassinoids, polyketides, and highly rearranged limonoids910111213. Recently, unprecedented quassinoids and limonoid derivatives with notable biological properties have been discovered and evaluated by our group141516. As part of our continuous effort to search for bioactive natural products17181920, two new 16-nor limonoids, harperspinoids A and B ( 1 and 2 ), with a unique 7/5/5/6/5 ring system, as well as a known one, Harperforin G ( 3 ), were isolated from the aerial parts of the title plant (Fig.…”

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confidence: 99%

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Yan

Cao

et al. 2016

Sci Rep

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Two new 16-nor limonoids, harperspinoids A and B (1 and 2), with a unique 7/5/5/6/5 ring system, have been isolated from the plant Harrisonia perforate together with a known one, Harperforin G (3). Their structures were elucidated by NMR spectroscopy, X-ray diffraction analysis and computational modelling. Compound 1 exists as polymorphic crystals. Conformations of 1 in solution were further discussed based on the computational results. These compounds exhibited notable inhibitory activity against the 11β-HSD1 enzyme. Compound 3 had potencies for the inhibition of human 11β-HSD1 with high selectivity against 11β-HSD2 (IC50 0.58 μM, SI > 174). Molecular docking and quantitative structure-activity relationship studies revealed a mixed regulatory mechanism.

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confidence: 99%

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Yan

Cao

et al. 2016

Sci Rep

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“…In the next step, palladium-catalyzed decarboxylative asymmetric allylic alkylation was performed using a ligand 25 developed by Trost to provide access to α-alkynyl α-allyl ketones with up to 97% ee. 53 , fragments of azadirachtin 54 and retigeranic acid 55 , and perforanoid A 56 . The latter report is interesting because, for the first time, the alkynylation was not performed starting from an isolated β-ketoester but rather on the enolate generated in situ through methoxycarbonylation of lactone 26, to furnish directly alkynylated product 27 (equation 4).…”

Section: Alkynylation Reactionsmentioning

confidence: 99%

“…56). A similar strategy was applied to the synthesis of fluorocyclopentenes 133-135 using fluoroalkylidenecarbenes by Hara and coworkers (equation 57)235 .…”

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confidence: 99%

Alkynylations and Vinylations

Hari

Nicolai

Waser

2018

Patai's Chemistry of Functional Groups

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Alkynes and alkenes are important building blocks in synthetic organic chemistry and related domains. Therefore, unceasing efforts have been invested to develop new methods to introduce these valuable functional groups. Traditionally, most alkynylation and alkenylation reactions have relied on the use of olefins and acetylenes as nucleophilic reacting species, limiting the accessible structural diversity. The discovery of the unique properties of hypervalent iodine has more recently significantly broadened the scope of electrophilic ethynylation and vinylation reactions. Alkynyl and alkenyl iodonium salts were first recognized as powerful reagents to install electrophilic acetylenes and olefins onto nucleophilic substrates under mild conditions. Their low stability has however narrowed the area of their applications. Since 2009, more stable cyclic benziodoxol(on)e reagents have shown their superiority as effective electrophilic alkynylating and alkenylating reagents in numerous metal-free and metal-catalyzed olefination and ethynylation reactions of carbon centered nucleophiles, radicals, and heteroatom nucleophiles. In this chapter, an overview of the progress in the field is presented, including a short summary of pioneering works, followed by a more in-depth description of recent results.

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“…Since 1991, the Hao’s team has studied the chemical components of more than 200 species of plants and identified more than 4600 chemical constituents including 1400 new structures and 90 new scaffolds, part of which were cited by “Hot off the Press” in Natural Product Reports (Fig. 1 ) [ 1 – 32 ]. The studies include the elucidation of complex chemical structures, exotic and novel backbones, and novel biogenetic mechanisms for Daphniphyllum alkaloids.…”

Section: Mining Novel Phytochemical Structures From Diverse Plants Inmentioning

confidence: 99%

An Explorer of Chemical Biology of Plant Natural Products in Southwest China, Xiaojiang Hao

Shen

Chen

2018

Nat. Prod. Bioprospect.

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Xiaojiang Hao, who obtained Master Degree from Kunming Institute of Botany (KIB), Chinese Academy of Sciences (CAS) in 1985, and Doctor in Pharmacy degree in Pharmacy from Institute for Chemical Research, Kyoto University, in 1990, was born in Chongqing in July, 1951. In 1991, he returned to KIB, CAS, as an Associate professor and served as the chair of the Department of Phytochemistry. In 1994, he was promoted to a full professor at the current institute. He served as the Deputy Director of KIB and the Director of Open Laboratory of Phytochemistry from 1995 to 1997, and the Director of KIB from 1997 to 2005. Professor Hao has published more than 450 peer-reviewed SCI papers, which have been cited over 6000 times. He has obtained one PCT patent and 23 patents in China. Due to his tremendous efforts, one candidate drug, phenchlobenpyrrone, has entered the Phase II clinical trail for the treatment of Alzheimer’s disease. Moreover, he won the First Prize of Natural Sciences in Yunnan Province for three times, and Ho Leung Ho Lee Fund Science and Technology Innovation Award in 2017.Graphical Abstract

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Isolation and Asymmetric Total Synthesis of Perforanoid A

Cited by 65 publications

References 68 publications

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Alkynylations and Vinylations

An Explorer of Chemical Biology of Plant Natural Products in Southwest China, Xiaojiang Hao

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