Flexible Approach to <i>Stemona</i> Alkaloids: Total Syntheses of (−)-Stemospironine and Three New Diastereoisomeric Analogs

Bardají, Nuria; Sánchez-Izquierdo, Francisco; Alibés, Ramón; Font, Josep; Busquè, Félix; Figueredo, Marta

doi:10.1021/ol302185j

Cited by 13 publications

(4 citation statements)

References 34 publications

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“…In 2014, Yang and coworkers published concise total syntheses of both (AE)-tuberostemospiroline (29g) and In 2011, Figueredo and coworkers disclosed an asymmetric total synthesis of (−)-stemospironine (29k) from aldehyde 29j in which an intramolecular Wadsworth-Emmons olenation was exploited as the key C-C bond-forming reaction to install the spirocyclic C-ring (Scheme 16B). 97 2.6.1 Outlook. Total syntheses of the majority of tubersostemospironine alkaloids have yet to be completed (Fig.…”

Section: Tuberostemospironine Classmentioning

confidence: 99%

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Strategies for the synthesis ofStemonaalkaloids: an update

et al. 2022

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Section: Tuberostemospironine Classmentioning

confidence: 99%

“…In 2011, Figueredo and coworkers disclosed an asymmetric total synthesis of (−)-stemospironine ( 29k ) from aldehyde 29j in which an intramolecular Wadsworth–Emmons olefination was exploited as the key C–C bond-forming reaction to install the spirocyclic C-ring (Scheme 16B). 97…”

Section: Synthesis Of Stemona Alkaloids and Related Compoundsmentioning

confidence: 99%

Strategies for the synthesis ofStemonaalkaloids: an update

et al. 2022

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“…Another synthesis of the croomine-type alkaloid was Figueredo's work on (-)-stemospironine (3) [28], largely based on their previous efforts towards the proposed structure of stemonidine [29]. The key feature was the application of an intramolecular Horner-Wadsworth-Emmons (HWE) olefination to afford the requisite spiro--lactone (Scheme 9).…”

Section: Croomine-typementioning

confidence: 99%

Recent Advances in the Synthesis of Stemona Alkaloids

Liu

Wang

2015

Natural Product Communications

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Stemona alkaloids, featuring polycyclic structures and interesting bioactivities, constitute a distinct class from the Stemonaceae family. In this review, recent advances in the synthesis of these unique alkaloids are briefly discussed, highlighting the application of novel synthetic strategies to access the core structures, as well as creative solutions to the installation of multiple stereogenic centers. The literature reviewed in this article covers the publications from 2010 to November 2014, a period that witnessed the prosperity of the synthesis of Stemona alkaloids.

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“…It has been used to treat eczema, scabies, pertussis, and other illnesses [ 1 ]. In East and Southeast Asia, extracts from Stemona tuberosa Lour are employed as household insecticides and as a treatment for respiratory ailments [ 2 ]. The roots of Stemona tuberosa Lour possess medicinal properties, which include lung moisturization and cough relief.…”

Section: Introductionmentioning

confidence: 99%

Study of the Structure and Bioactivity of Polysaccharides from Different Parts of Stemona tuberosa Lour

Qiu,

Ou,

et al. 2024

Molecules

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The polysaccharides from Stemona tuberosa Lour, a kind of plant used in Chinese herbal medicine, have various pharmacological activities, such as anti-inflammatory and antioxidant properties. However, the effects of the extraction methods and the activity of polysaccharides from different parts are still unknown. Therefore, this study aimed to evaluate the effects of different extraction methods on the yields, chemical compositions, and bioactivity of polysaccharides extracted from different parts of Stemona tuberosa Lour. Six polysaccharides were extracted from the leaves, roots, and stems of Stemona tuberosa Lour through the use of hot water (i.e., SPS-L1, SPS-R1, and SPS-S1) and an ultrasound-assisted method (i.e., SPS-L2, SPS-R2, and SPS-S2). The results showed that the physicochemical properties, structural properties, and biological activity of the polysaccharides varied with the extraction methods and parts. SPS-R1 and SPS-R2 had higher extraction yields and total sugar contents than those of the other SPSs (SPS-L1, SPS-L2, SPS-S1, and SPS-S2). SPS-L1 had favorable antioxidant activity and the ability to downregulate MUC5AC expression. An investigation of the anti-inflammatory properties showed that SPS-R1 and SPS-R2 had greater anti-inflammatory activities, while SPS-R2 demonstrated the strongest anti-inflammatory potential. The results of this study indicated that SPS-L1 and SPS-L2, which were extracted from non-medicinal parts, may serve as potent natural antioxidants, but further study is necessary to explore their potential applications in the treatment of diseases. The positive anti-inflammatory effects of SPS-R1 and SPS-R2 in the roots may be further exploited in drugs for the treatment of inflammation.

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Flexible Approach to Stemona Alkaloids: Total Syntheses of (−)-Stemospironine and Three New Diastereoisomeric Analogs

Cited by 13 publications

References 34 publications

Strategies for the synthesis ofStemonaalkaloids: an update

Strategies for the synthesis ofStemonaalkaloids: an update

Recent Advances in the Synthesis of Stemona Alkaloids

Study of the Structure and Bioactivity of Polysaccharides from Different Parts of Stemona tuberosa Lour

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