Synthetic Strategy toward the Pentacyclic Core of <i>Melodinus</i> Alkaloids

Goli, Navya; Kallepu, Shivakrishna; Mainkar, Prathama S.; Lakshmi, Jerripothula K.; Chegondi, Rambabu; Chandrasekhar, Srivari

doi:10.1021/acs.joc.7b03138

Cited by 23 publications

(13 citation statements)

References 38 publications

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“…By employing an RCM reaction at the end of their synthesis, the group of Chandrasekhar revelead the construction of meloscine pentacyclic core 578 (Scheme 87). Meloscine is an alkaloid produces by plant Melodinus scandens Forst, this alkaloid and other members of this family are traditional medicine for treatment of inflammation in China [268] . In this synthetic strategy, the Povarov reaction between aniline 572 , cyclopentadiene 573 , and ethyl glyoxalate 574 in presence of ceric ammonium nitrate (CAN) afforded a tryclic compound 575 , which was further converted to a tetracyclic ketone 576 in several steps.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

“…Meloscine is an alkaloid produces by plant Melodinus scandens Forst, this alkaloid and other members of this family are traditional medicine for treatment of inflammation in China. [268] In this Sabitha and co-workers presented the linear synthesis of aspergillide D macrocycle core 581 involving the RCM reaction as a key step (Scheme 88). Aspergillide D is a 16-membered marine macrolide, isolated from fungal strain Aspergillussp.…”

Section: Studies Towards Fragment Syntheses Of Natural Products Based...mentioning

confidence: 99%

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Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Section: Studies Towards Fragment Syntheses Of Natural Products Based...mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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“…The Povarov reaction and its variants can be catalyzed by a wide variety of Brønsted and Lewis acids: BF 3 ·Et 2 O, 33 34 35 36 37 38 39 40 BiCl 3 , 41–44 CAN, 45 46 47 48 49 50 51 cerium sulfate, 52 Amberlyst 15, 53 phthalic acid, 54 p -toluenesulfonic acid 55 56 and its supramolecular analogue CX4SO 3 H, 57 ferric sulfate, 58 59 60 iodine, 61 62 63 InCl 3 , 64 65 66 67 68 69 NH 4 Br, 70 Sc(OTf) 3 , 71 72 73 74 75 and Sc(III)-loaded resin, 76 Y(OTf) 3 , 77 78 79 80 81 bistriflimide, 28 TFA 82 and zinc chloride. 83 Moreover, mixed catalytic systems may be employed, such as Ca(OTf) 2 /Bu 4 NPF 6 84 and CeCl 3 /NaI.…”

Section: Tetrahydroquinolinesmentioning

confidence: 99%

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

et al. 2022

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Multicomponent Povarov reaction is a powerful approach for the construction of N-heterocyclic containing substances. By using Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form, respectively, two new Csp3-Csp3 and one Csp3-Nsp3 bonds, two new Csp2-Csp2 and one Csp2-Nsp2 bonds and four Csp3-Csp3 and two Csp3-Nsp1 bonds. This review article reports the main features of the Povarov reaction such as its mechanism, the scope of such reaction concerning to different catalysts and substrates used on it as well as the stereoselective versions of Povarov reaction

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“…In pursuit of a synthesis of meloscine alkaloids stereoselective radical annulations of divinylcyclopropanes have been developed . Moreover three‐component Povarov reactions were employed as key step to build the quinolone frame of the Melodinus alkaloids meloscine, scandine, and epimeloscine …”

Section: Introductionmentioning

confidence: 99%

A Highly Enantio‐ and Diastereoselective Synthesis of Spirocyclic Dihydroquinolones via Domino Michael Addition‐Lactamization of ortho‐Quinone Methide Imines

Hodík

Schneider

2018

Chemistry A European J

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Spirocyclic dihydroquinolones have been obtained with good yields and excellent diastereoselectivity (> 20:1 d.r.), and enantioselectivity (up to 99:1 e.r.) from in situ generated ortho-quinone methide imines and cyclic b-oxo esters. This one-step domino Michael addition-lactamization processf eatures mild reactionc onditions, easily accessible startingm aterials, and products with two adjacent chiral centers one of whichi sq uaternary.M echanistic studies revealedthe in situ generatedc hiralm agnesium phosphate salt rather than the free phosphoric acid to be the more reactive catalystfor this reaction.

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Synthetic Strategy toward the Pentacyclic Core of Melodinus Alkaloids

Cited by 23 publications

References 38 publications

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Metathesis Reactions in Natural Product Fragments and Total Syntheses

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

A Highly Enantio‐ and Diastereoselective Synthesis of Spirocyclic Dihydroquinolones via Domino Michael Addition‐Lactamization of ortho‐Quinone Methide Imines

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