Asymmetric Total Syntheses of (−)-Jerantinines A, C, and E, (−)-16-Methoxytabersonine, (−)-Vindoline, and (+)-Vinblastine

Wang, Nengzhong; Liu, Jianrong; Wang, Chen; Bai, Leiyang; Jiang, Xuefeng

doi:10.1021/acs.orglett.7b03694

Cited by 60 publications

(23 citation statements)

References 43 publications

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“…Moreover, thiolactam structural unit plays a vital role as an active functional group in organic chemical transformations, which has been applied for the formation of C-C bond [2] and C=C bond [3] as well as the construction of complex compounds such as jerantinine. [4] However, limited methods have been developed for the synthesis of thiolactam due to the special structure with C=S bond (Figure 1b). [5] The conventional methods scarcely avoid the utilization of Lawesson reagent or its analogues for transforming carbonyl to thiocarbonyl with the defect of low atomic and environment economy, sometimes with high temperature and by-products that are difficult to separate.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

2019

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Summary of main observation and conclusion We report herein a protocol for thiolactam preparation with potassium sulfide via visible‐light‐mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

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Section: Background and Originality Contentmentioning

confidence: 99%

Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

2019

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“… A [4+2] cycloaddition and α,β‐unsaturated ketone indolization rearrangement to tetracyclic indolines 119 (Jiang et al …”

Section: Diels–alder Reactionsmentioning

confidence: 99%

“…+2] cycloaddition and a,b-unsaturated ketone indolization rearrangement to tetracyclic indolines 119 (Jiang et al [39] ). boxylation,DIBAL-Hreduction and Wittig olefination.…”

Section: Scheme14 A[ 4 +mentioning

confidence: 99%

Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids

Wang

Xie

Lin

et al. 2018

Chemistry A European J

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Indole alkaloids bearing the tetracyclic indoline scaffolds of 1H-pyrrolo[2,3-d]carbazole have shown fascinating chemical diversity and significant biological activities. The development of efficient synthetic methodologies for such a tetracyclic scaffold remains highly desirable in both synthetic chemistry and medicinal chemistry. This review outlines key strategies for the construction of the tetracyclic indoline scaffolds in total syntheses of many indole alkaloids. The key strategies include nucleophilic additions, Diels-Alder reactions, radical cyclizations, and palladium-catalyzed coupling reactions. The representative examples and their applications in the total syntheses are described here and discussed in depth.

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“…S10c [18]]. The low-temperature field-effect mobility reached up to 5.2 cm 2 =Vs, far exceeding pentacene polycrystalline thinfilm devices at similar temperatures [10,50]. The bandlike behavior could extend down to our base temperature of 50 K at high carrier density [ Fig.…”

Section: Prl 116 016602 (2016) P H Y S I C a L R E V I E W L E T T Ementioning

confidence: 99%

“…While the mobility of bulk organic semiconductors has increased dramatically [1][2][3], an outstanding issue is to directly examine the structure-property relationship at the semiconductor-dielectric interface [4], where charge transport actually occurs [5][6][7]. Ultrathin organic semiconductors a few nanometers thick are often dominated by traps and disorders and far away from the intrinsic transport regime [8][9][10]. Another challenge in organic electronics is the development of layer-by-layer epitaxy with precision similar to molecular beam epitaxy in their inorganic counterparts [11].…”

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confidence: 99%

Precise Layering of Organic Semiconductors

Natelson

2016

Physics

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One of the basic assumptions in organic field-effect transistors, the most fundamental device unit in organic electronics, is that charge transport occurs two dimensionally in the first few molecular layers near the dielectric interface. Although the mobility of bulk organic semiconductors has increased dramatically, direct probing of intrinsic charge transport in the two-dimensional limit has not been possible due to excessive disorders and traps in ultrathin organic thin films. Here, highly ordered single-crystalline monoto tetralayer pentacene crystals are realized by van der Waals (vdW) epitaxy on hexagonal BN. We find that the charge transport is dominated by hopping in the first conductive layer, but transforms to bandlike in subsequent layers. Such an abrupt phase transition is attributed to strong modulation of the molecular packing by interfacial vdW interactions, as corroborated by quantitative structural characterization and density functional theory calculations. The structural modulation becomes negligible beyond the second conductive layer, leading to a mobility saturation thickness of only ∼3 nm. Highly ordered organic ultrathin films provide a platform for new physics and device structures (such as heterostructures and quantum wells) that are not possible in conventional bulk crystals. DOI: 10.1103/PhysRevLett.116.016602 Organic field-effect transistors (OFETs) offer unique advantages of low cost, light weight, and flexibility and are widely used in the electronics and display industry. While the mobility of bulk organic semiconductors has increased dramatically [1][2][3], an outstanding issue is to directly examine the structure-property relationship at the semiconductor-dielectric interface [4], where charge transport actually occurs [5][6][7]. Ultrathin organic semiconductors a few nanometers thick are often dominated by traps and disorders and far away from the intrinsic transport regime [8][9][10]. Another challenge in organic electronics is the development of layer-by-layer epitaxy with precision similar to molecular beam epitaxy in their inorganic counterparts [11]. These challenges may be alleviated if molecular crystals are processed into large-area, highly crystalline monolayers. Such a 2D form factor will also bring about new applications such as nanoporous membranes and insulating dielectrics [12,13]. Several recent breakthroughs in various types of 2D organic materials such as polymers [14,15], oligomers [16], and covalent organic frameworks [17] have already shown great promise in this direction. However, one of the most fundamental questions regarding the nature of charge transport at the 2D limit has not been addressed. In this work, we study the benchmark molecule pentacene, epitaxially crystallized on a BN substrate because of its high mobility and simple structure to model. The highly clean system allows us to provide the first definitive scenario of how molecular packing and charge transport are modulated near the interface, without being dominated by extrinsic factors. Our...

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Asymmetric Total Syntheses of (−)-Jerantinines A, C, and E, (−)-16-Methoxytabersonine, (−)-Vindoline, and (+)-Vinblastine

Cited by 60 publications

References 43 publications

Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids

Precise Layering of Organic Semiconductors

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Asymmetric Total Syntheses of (−)-Jerantinines A, C, and E, (−)-16-Methoxytabersonine, (−)-Vindoline, and (+)-Vinblastine

Cited by 60 publications

References 43 publications

Visible‐Light‐Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

Visible‐Light‐Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids

Precise Layering of Organic Semiconductors

Contact Info

Product

Resources

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Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

Visible‐Light‐Mediated C(sp³)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide