A Ten‐Step Total Synthesis of Speradine C

Liu, Haichao; Chen, Lijun; Yuan, Kun; Jia, Yanxing

doi:10.1002/ange.201902004

Cited by 8 publications

(5 citation statements)

References 53 publications

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“…The main outcomes of this study were the construction of four cyclic rings in three cyclization steps, an [3 + 2] annulation for the formation of C and D rings, an N-Chlorosuccinimide (NCS)-assisted oxidative formation of the E ring, and a Ru-catalyzed ketohydroxylation to build the F ring. [50] Propindilactone G is a highly oxygenated polycyclic Schisandranortriterpenoids (or schinortriterpenoids). It was discovered by Sun and co-workers from plants of the Schisandraceae.…”

Section: (à )-Sinularianin B (14)mentioning

confidence: 99%

“…The first ten steps synthesis of speradine C was completed from an economically accessible 4‐bromoindole intermediate (Scheme ). The main outcomes of this study were the construction of four cyclic rings in three cyclization steps, an [3+2] annulation for the formation of C and D rings, an N ‐Chlorosuccinimide (NCS)‐assisted oxidative formation of the E ring, and a Ru‐catalyzed ketohydroxylation to build the F ring …”

Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%

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Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Section: (à )-Sinularianin B (14)mentioning

confidence: 99%

Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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“…[25] Speradines C (VIII), an α-cyclopiazonic acid-derived natural alkaloid received a tremendous application in total synthesis owing to the existence of an unprecedented hexacyclic ring system with six stereogenic centers in its core structure. [26] A part from these natural products, the five-membered spirocyclic oxindoles possess diverse therapeutic applications (Figure 1b). MI-219 (IX) is reported to disrupt the binding of p53 tumor suppressor and murine double minute 2 (MDM2), thereby accelerating p53 activation and inhibition of tumor cell growth.…”

Section: Introductionmentioning

confidence: 99%

“…The naturally occurring hemiterpene spirooxindole, Elacomine ( VII ) was isolated from Elaeagnus commutate and proved to be toxic to melanoma cells [25] . Speradines C ( VIII ), an α‐cyclopiazonic acid‐derived natural alkaloid received a tremendous application in total synthesis owing to the existence of an unprecedented hexacyclic ring system with six stereogenic centers in its core structure [26] …”

Section: Introductionmentioning

confidence: 99%

Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

2023

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Spirocyclic compounds, particularly spirooxindoles that comprise a tetrahedral sp3‐hybridized carbon atom at the C‐3 position of an orthogonally shaped bicyclic structure have recently received increasing attention in drug discovery and development, besides their major potential in natural products and synthetic organic chemistry. They are found to be the major structural constituents of many alkaloids, and key active building blocks for the construction of various pharmaceutically significant molecules. On the other hand, with the increasing awareness of people about protecting their health and the living environment from the pollution caused by chemical laboratories and industry, the development of a synthetic method that provides alternatives to the traditional one by introducing atom economical sustainable processes is of scientifically and technically demanding but challenging. To address these concerns and inspired by the natural photosynthesis process, recently visible light‐induced chemistry appears to be a highly economic, sustainable, and alternative approach to organic synthesis. The present mini‐review aims to highlight the recent progress accomplished in the straightforward construction of spirooxindoles accelerated by visible light irradiation from the period of 2015 to date. Besides reviewing the advantages achieved in this field, we also attempt to find out the drawback, mechanistic rationalization, and scopes of future applications.

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“…Recently, transition-metal-catalyzed direct CÀ H activation reactions have been extensively studied on account of its high step-and atom-economic performances. [5] Driven by the conspicuous importance of C4-substituted indole derivatives in heteroatomic natural products and medicinal science (Scheme 1a), [6] many research groups have focused on exploiting direct functionalization reaction of indoles at the relatively less explored C-4 positions using CÀ H activation strategy. Along this line, with the aid of the weakly coordinating groups such as the carbonyl and thioether installed at the C3 position, the regioselective CÀ H functionalization at the C-4 position of indoles has been achieved successfully.…”

mentioning

confidence: 99%

Rhodium(III)‐Catalyzed Regioselective C−H Allylation and Prenylation of Indoles at C4‐Position

et al. 2021

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Herein, Rh(III)-catalyzed C4-selective CÀ H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished.

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A Ten‐Step Total Synthesis of Speradine C

Cited by 8 publications

References 53 publications

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

Rhodium(III)‐Catalyzed Regioselective C−H Allylation and Prenylation of Indoles at C4‐Position

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