Total synthesis of the antibacterial polyketide natural product thailandamide lactone

Sharma, Himangshu; Mondal, Joyanta; Ghosh, Ananyo K; Pal, Ritesh Ranjan; Goswami, Rajib Kumar

doi:10.1039/d2sc04727f

Cited by 10 publications

(2 citation statements)

References 44 publications

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“…Dipeptide 9 was subjected to Fmoc deprotection and subsequently coupled with the corresponding acid obtained from dipeptide 10 (by hydrogenation) using HATU/HOAt/DIPEA to get tetrapeptide 11 in good overall yield. On the other hand, commercially available dodecanal was subjected to Crimmins acetate aldol − using the known thiazolidinethione 12 in the presence of TiCl 4 /DIPEA to obtain aldol products 13a and 13b as the major and minor isomers ( dr = 7:3), respectively. Purified major isomer 13a was then transmuted to compound 8 using benzyl alcohol (BnOH) and DMAP.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy

Auddy,

Gupta,

Mandi

et al. 2024

ACS Med. Chem. Lett.

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A convergent strategy for the first total synthesis of the lipopeptide bacilotetrin C has been developed. The key features of this synthesis include Crimmins acetate aldol, Steglich esterification, and macrolactamization. Twenty-nine variants of the natural product were prepared following a systematic structure−activity relationship study, where some of the designed analogues showed promising cytotoxic effects against multiple human carcinoma cell lines. The most potent analogue exhibited a ∼37-fold enhancement in cytotoxicity compared to bacilotetrin C in a triple-negative breast cancer (MDA-MB-231) cell line at submicromolar doses. The study further revealed that some of the analogues induced autophagy in cancer cells to the point of their demise at doses much lower than those of known autophagy-inducing peptides. The results demonstrated that the chemical synthesis of bacilotetrin C with suitable improvisation plays an important role in the development of novel anticancer chemotherapeutics, which would allow future rational design of novel autophagy inducers on this template.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy

Auddy,

Gupta,

Mandi

et al. 2024

ACS Med. Chem. Lett.

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“…The major problems lay in the global deprotection of the protecting groups and the selective reduction of the olefin in the long hydrophobic chain in the presence of other requisite olefins . The structural complexity, bioactivity, unsolved synthetic challenges, and our interest in natural product chemistry prompted us to embark on their total synthesis. We initially envisaged the asymmetric synthesis of sorangiolide A. Herein, we disclose a flexible and convergent synthetic route for the first successful total synthesis of the target natural product and illuminate its possible forms of existence in the solution phase.…”

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confidence: 99%

Total Synthesis of Antibacterial Macrolide Sorangiolide A

Sahana,

Paul,

Sharma

et al. 2023

Org. Lett.

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A convergent route for the asymmetric total synthesis of antibacterial macrolide sorangiolide A has been developed for the first time. The key feature of this synthesis includes Krische iridium-catalyzed anti-diastereoselective carbonyl crotylation, Crimmins acetate aldol, Yamaguchi esterification, Julia−Kocienski olefination, Horner−Wadsworth−Emmons olefination, and ring-closing metathesis. The origin of the low intensity of the 13 C{ 1 H} NMR signals of the C1 and C2 centers of the natural product has been investigated, disclosing possible forms of existence for the natural product in the solution phase.

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Visible‐Light‐Driven Method for the Selective Synthesis of Amides and N‐Acylureas from Carboxylic Acids and Thioureas

Zhong,

Yang,

Liu

et al. 2024

Chemistry A European J

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In this work, we developed a visible‐light‐driven method for the selective synthesis of amides and N‐acylureas from carboxylic acids and thioureas. This protocol was featured as avoidance of additional oxidants and transition metal catalysts, simple manipulations, low cost, broad substrate scope, and good functional group tolerance. As only oxygen serves as the oxidation reagent, this method provides a promising synthesis candidate for the formation of N‐aryl amides and N‐acylureas, including late‐stage functionalization of complex pharmaceutical molecules and biologically active molecules.

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Total synthesis of the antibacterial polyketide natural product thailandamide lactone

Abstract: Stereoselective total synthesis of structurally intriguing polyketide natural product thailandamide lactone has been accomplished for the first time adopting a convergent approach. The key feature of this synthesis includes Crimmins...

Cited by 10 publications

References 44 publications

Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy

Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy

Total Synthesis of Antibacterial Macrolide Sorangiolide A

Visible‐Light‐Driven Method for the Selective Synthesis of Amides and N‐Acylureas from Carboxylic Acids and Thioureas

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