Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Ebner, Christian; Carreira, Erick M.

doi:10.1002/ange.201505126

Cited by 17 publications

(4 citation statements)

References 41 publications

(19 reference statements)

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“…Indeed, with 4–6 rings, 7–10 contiguous stereocenters, and 2 quaternary stereocenters, these challenging terpenoid isolates are an ideal proving ground for the development of unique strategies and methods. Two elegant approaches to the synthesis of pallambins have appeared, one from the Wong group 2 and the other from the Carreira 3 group. The former route furnished 3 and 4 in 38 steps from the Wieland–Miescher ketone, and the latter afforded 1 and 2 in 23 steps from a fulvene.…”

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confidence: 99%

11-Step Total Synthesis of Pallambins C and D

et al. 2016

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The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.

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confidence: 99%

11-Step Total Synthesis of Pallambins C and D

et al. 2016

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“…[244] Pallambins A-D, extracted from the epilithic liverwort Pallavicinia ambigua, [245] show no important biological activity. Wong et al [246] demonstrated the formation of pallambins C (265) and D (266) in 38 steps from the Wieland-Miescher ketone. [247] Baran et al in 2016 reported an 11-step pathway to ( 265) and ( 266), in which 9 of the 11 steps are strategic and masking substituent manipulations are absent.…”

Section: Terpenoidsmentioning

confidence: 99%

“…Pallambins A‐D, extracted from the epilithic liverwort Pallavicinia ambigua , [245] show no important biological activity. Wong et al [246] . demonstrated the formation of pallambins C ( 265 ) and D ( 266 ) in 38 steps from the Wieland‐Miescher ketone [247] .…”

Section: Applications Of Robinson Annulation In the Total Synthesis O...mentioning

confidence: 99%

Robinson Annulation Applied to the Total Synthesis of Natural Products

et al. 2023

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The Robinson annulation is a significant reaction for the synthesis of α,β‐unsaturated ketone ring including the generation of two C−C bonds. It involves a Michael addition of a ketone and a methyl or ethyl vinyl ketone with subsequent intramolecular aldol condensation. Natural products and their structurally related analogues have historically made a major contribution to pharmacotherapy, particularly for cancer and infectious diseases. The Robinson annulation has frequently been employed as a vital step in the total synthesis of these important naturally occurring compounds and related complex biologically active products. In this review, we try to underscore the applications of the Robinson annulation in the total synthesis of biologically active natural products.

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“…In 2015, Carreiraa nd co-workers creativelyd eveloped aD iels-Alder reactiono fp entafulvene with acrylate to construct the bridged bicyclo[2.2.1] system,w hich represents the first application of pentafulvene-participated cycloaddition reactioni n complex natural product total synthesis. [56] By the use of Trost's two-step protocol [57] involving hydride reduction and Hoffman elimination on stable amine 115,t he highly unstable pentafulvene 116 was prepared and utilized in situ for the desired [4+ +2] cycloaddition with acrylate. Et 2 AlCl was the optimal Lewis acid catalystf or this cycloaddition to smoothly and stereoselectively generate the bridged [2.2.1] cycloadduct 117.…”

Section: Total Synthesis Of Pallambinsaand Bbyr H-catalyzed Càh Insermentioning

confidence: 99%

The Total Synthesis of Diquinane‐Containing Natural Products

Zhang

She

2021

Chemistry A European J

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Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane‐containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane‐containing natural product synthesis is provided.

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Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B

Cited by 17 publications

References 41 publications

11-Step Total Synthesis of Pallambins C and D

11-Step Total Synthesis of Pallambins C and D

Robinson Annulation Applied to the Total Synthesis of Natural Products

The Total Synthesis of Diquinane‐Containing Natural Products

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