Total Synthesis and Structural Revision of Antibiotic CJ‐16,264

Nicolaou, K. C.; Shah, Akshay; Korman, Henry; Khan, Tabrez; Shi, Lei; Worawalai, Wisuttaya; Theodorakis, Emmanuel A.

doi:10.1002/ange.201504337

Cited by 13 publications

(4 citation statements)

References 40 publications

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“…Indeed, arrival at 14 and 15 also helped in securing the relative stereochemical assignment in all the crucial intermediates during the course of the synthetic journey, as they were found to be spectroscopically in complete agreement with the data reported by others in the racemic form [7b] . Eventually, the deoxygenation in 14 and 15 were executed effortlessly via the Zn mediated reductive cleavage [16] of their respective mesylate derivatives in the presence of NaI in refluxing DME to access the chiral tetralins 2 a and 2 b .…”

Section: Resultssupporting

confidence: 79%

Total Synthesis of (−)‐Magnoshinin and (+)‐Merrilliaquinone: Application of a Late‐Stage Oxidative Functionalization Protocol

et al. 2022

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A unified approach for the first enantioselective total synthesis of magnoshinin and merrilliaquinone is reported. The key feature of the synthesis is the DDQ assisted chemoselective late‐stage oxidative functionalization of the polyoxygenated chiral tetralin core accessed by utilizing the relayed asymmetric induction strategy. Then, the follow‐up of chemoselective redox chemistry facilitates the synthesis of (−)‐magnoshinin (28.2 % overall yield) and (+)‐merrilliaquinone (20.6 % overall yield) along the shortest route, starting from the known 3‐(2,4,5‐trimethoxyphenyl)propanoic acid.

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Section: Resultssupporting

confidence: 79%

Total Synthesis of (−)‐Magnoshinin and (+)‐Merrilliaquinone: Application of a Late‐Stage Oxidative Functionalization Protocol

et al. 2022

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“…Scheme 4 shows a good example of the ability of this approach applied to the total synthesis of CJ-16,264, an antibiotic of fungal origin with impressive activity against several drug-resistant bacteria. 7 The synthesis involved the preparation of a macrocyclic diester containing the required diene and dienophile moieties and that was synthesized as enantiopure material from citronellal. A double transannular Diels–Alder reaction took place after heating to 220 °C in xylene, providing the exo -adduct in 48% yield.…”

Section: Transannular Cycloadditions and Electrocyclizationsmentioning

confidence: 99%

Recent Developments in Transannular Reactions

Reyes¹,

Prieto²,

Carrillo³

et al. 2022

Synthesis

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Transannular reactions have shown a remarkable performance for the construction of polycyclic scaffolds from medium- or large sized cyclic molecules in an unconventional manner. Recent examples of transannular reactions reported from 2011 have been reviewed, emphasizing the excellent performance of this approach when accessing the target compounds. This review also highlights how this methodology provides an alternative approach to other commonly used methodologies for the construction of cyclic entities such as cyclization or cycloaddition reactions

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“…40,41,[83][84][85][86][87] The third category includes molecules whose originally reported structure was later challenged based on biosynthetic considerations 88 [e.g., maitotoxin (74), Figure 7, stereogenic centers within gold-colored oval] and later confirmed by us as the correct one. 89 The fourth, and most common, category of structural elucidation through total synthesis is that involving revision of one or more stereochemical configurations and/or structural motifs (functional groups) [e.g., 21, 120, and 121 (Figure 14e), [90][91][92][93][94][95] 22 (Figure 14g), 85,86 24 (Figure 14h), [96][97][98] 30 and 31 (Figure 14n), [99][100][101][102][103] 33 (Figure 14j), 104 37 (Figure 14o), [105][106][107] 39 (Figure 14p), 108,109 44 (Figure 14r), 110 46 (Figure 14q), 111 47 (Figure 14s),…”

Section: Confirming Disproving Predicting and Revising Molecular Structures Of Natural Productsmentioning

confidence: 99%

Total Synthesis Endeavors and Their Contributions to Science and Society: A Personal Account

Nicolaou

Rigol

2019

CCS Chem

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The advent of organic synthesis in the 19th century, serendipitous as it was, set in motion a revolution in science that continues to evolve into increasing levels of sophistication and to expand into new domains of science and technology for the benefits of science and society. Its evolution was always driven by the challenges posed by natural products, whose structures were becoming increasingly complex and diverse. In response to these challenges, synthetic organic chemists were prompted to sharpen their art to reach their target molecules, whose structures were often confirmed only after their synthesis in the laboratory through the art and science of total synthesis. The latter became the “locomotive” and the “flagship” of organic synthesis, for through this practice novel synthetic methods were discovered and invented, and also tested for their generality, applicability, and scope with regard to molecular complexity and diversity. The purpose of total synthesis has also evolved over the years to include aspects beyond the synthesis of the molecule and confirmation of its structure. In this article, we briefly review the evolution of total synthesis in terms of its power and reach and demonstrate its current state of the art that combines fundamentals with translational aspects through examples from our laboratories. The highlighted examples reflect the newly emerged paradigm of the discipline that includes—in addition to the total synthesis of the target molecule—structural elucidations, method discovery and development, design, synthesis, and biological evaluation of analogues for biology and medicine, and training of young students, preparing them for academic and industrial careers in the various disciplines that require knowledge and skills to practice the central science of chemical synthesis. Such disciplines include chemical biology, drug discovery and development, materials science and nanotechnology, and other endeavors whose fundamentals depend and rely on the structure of the molecule and its synthesis.

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Total Synthesis and Structural Revision of Antibiotic CJ‐16,264

Cited by 13 publications

References 40 publications

Total Synthesis of (−)‐Magnoshinin and (+)‐Merrilliaquinone: Application of a Late‐Stage Oxidative Functionalization Protocol

Total Synthesis of (−)‐Magnoshinin and (+)‐Merrilliaquinone: Application of a Late‐Stage Oxidative Functionalization Protocol

Recent Developments in Transannular Reactions

Total Synthesis Endeavors and Their Contributions to Science and Society: A Personal Account

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