Ten-step asymmetric total syntheses of potent antibiotics anthracimycin and anthracimycin B

Tian, Peilin; Ye, Wenkang; Zhang, Xiayan; Tong, Yi; Qian, Pei‐Yuan; Tong, Rongbiao

doi:10.1039/d2sc05049h

Cited by 12 publications

(4 citation statements)

References 49 publications

(76 reference statements)

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“…First, after examining various Lewis acids, BF 3 ·Et 2 O was identified as a competent catalyst for promoting the IMDA reaction [ 22 ] of compound 5 . This resulted in desired product 3 in 59% yield on the gram scale with an excellent 9 : 1 diastereomeric ratio (Figure S2).…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram‐scale Synthesis of Ferroptosis Inducer Talaroconvolutin A

Yao,

Yang,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryThe first total synthesis of talaroconvolutin A (1.1 g obtained) and talarofuranone has been achieved using accessible materials (12 steps, 7.5% and 8.2% yields, respectively). Convergent routes involved intramolecular Diels−Alder reactions in two approaches for creating the decalin moiety. Additionally, an unprecedented DMP‐mediated domino reaction resulted in the deoxy‐tetramic acid system. These syntheses not only establish the absolute configuration of talaroconvolutin A but also enable further collaborative studies of this type of ferroptosis inducers.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram‐scale Synthesis of Ferroptosis Inducer Talaroconvolutin A

Yao,

Yang,

et al. 2024

Chin. J. Chem.

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“…However, a plethora of bioactive phytochemicals with an antibiotic-potentiating ability and reversing antibiotic resistance in B. anthracis have been identified ( Dassanayake et al, 2021 ). In addition, the discovery of potent new antibiotics such as anthracimycin with a novel mechanism of action (inhibiting DNA/RNA synthesis) and low toxicity to human cells represents a major advance in the field of antibiotics against B. anthracis helping to counter existing or future antibiotic resistance problems ( Tian et al, 2022 ). Moreover, three new siphophages that can specifically infect and lyse B. anthracis were recently isolated.…”

Section: Resultsmentioning

confidence: 99%

Anthrax revisited: how assessing the unpredictable can improve biosecurity

Sabra,

Krin,

Romeral

et al. 2023

Front. Bioeng. Biotechnol.

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B. anthracis is one of the most often weaponized pathogens. States had it in their bioweapons programs and criminals and terrorists have used or attempted to use it. This study is motivated by the narrative that emerging and developing technologies today contribute to the amplification of danger through greater easiness, accessibility and affordability of steps in the making of an anthrax weapon. As states would have way better preconditions if they would decide for an offensive bioweapons program, we focus on bioterrorism. This paper analyzes and assesses the possible bioterrorism threat arising from advances in synthetic biology, genome editing, information availability, and other emerging, and converging sciences and enabling technologies. Methodologically we apply foresight methods to encourage the analysis of contemporary technological advances. We have developed a conceptual six-step foresight science framework approach. It represents a synthesis of various foresight methodologies including literature review, elements of horizon scanning, trend impact analysis, red team exercise, and free flow open-ended discussions. Our results show a significant shift in the threat landscape. Increasing affordability, widespread distribution, efficiency, as well as ease of use of DNA synthesis, and rapid advances in genome-editing and synthetic genomic technologies lead to an ever-growing number and types of actors who could potentially weaponize B. anthracis. Understanding the current and future capabilities of these technologies and their potential for misuse critically shapes the current and future threat landscape and underlines the necessary adaptation of biosecurity measures in the spheres of multi-level political decision making and in the science community.

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“…[55][56][57] They are not dangerous to normal human cells and perform their biological activities effectively. Taking into account the high demand of non-resistible antibiotics, Tian et al 58 in 2022 devised a concise and efficient synthetic strategy for the synthesis of pharmaceutically important macrolides i.e. anthracimycin and anthracimycin B in 25 mg and 14 mg, respectively.…”

Section: Synthesis Of Macrolide Based Natural Productsmentioning

confidence: 99%

Mukaiyama aldol reaction: an effective asymmetric approach to access chiral natural products and their derivatives/analogues

Mushtaq,

Zahoor

2023

RSC Adv.

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Ten-step asymmetric total syntheses of potent antibiotics anthracimycin and anthracimycin B

Abstract: The rise of antibiotic resistance calls for the development of novel antibiotics with new molecular structure and new mode of action. However, in the past decades only a few novel...

Cited by 12 publications

References 49 publications

Total Synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram‐scale Synthesis of Ferroptosis Inducer Talaroconvolutin A

Total Synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram‐scale Synthesis of Ferroptosis Inducer Talaroconvolutin A

Anthrax revisited: how assessing the unpredictable can improve biosecurity

Mukaiyama aldol reaction: an effective asymmetric approach to access chiral natural products and their derivatives/analogues

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