An asymmetric synthesis of (R)-(+)-2-nonyl-2-(carbomethoxy) cyclopentanone, a known precursor of the antibiotic (−)-malyngolide

Guingant, André

doi:10.1016/s0957-4166(00)82165-5

Cited by 24 publications

(3 citation statements)

References 11 publications

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“…Several products on the list have the potential to serve as intermediates in the preparation of bioactive compounds. One such example is product 11 , which is a derivative of a well-established precursor of (+)-Malyngolide, an antibiotic that exhibits significant activity against Mycobacterium smegmatis and Streptococcus pyogenes . Product 19 , on the other hand, could potentially be used to synthesize Ptaquilosin, a compound that has shown antitumor activity and toxicity toward myelocytic leukemia .…”

Section: Resultsmentioning

confidence: 99%

“…One such example is product 11, which is a derivative of a well-established precursor of (+)-Malyngolide, an antibiotic that exhibits significant activity against Mycobacterium smegmatis and Streptococcus pyogenes. 25 Product 19, on the other hand, could potentially be used to synthesize Ptaquilosin, a compound that has shown antitumor activity and toxicity toward myelocytic leukemia. 26 In the case of an NHP ester that bears stereocenters at a remote position, the stereochemistry of the amine catalyst, rather than that of the NHP ester, controls the stereochemistry of the coupling product (products 20−23).…”

Section: ■ Introductionmentioning

confidence: 99%

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Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Li,

Zhang,

et al. 2024

J. Am. Chem. Soc.

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The catalytic and enantioselective construction of quaternary (all-carbon substituents) stereocenters poses a formidable challenge in organic synthesis due to the hindrance caused by steric factors. One conceptually viable and potentially versatile approach is the coupling of a C−C bond through an outer-sphere mechanism, accompanied by the realization of enantiocontrol through cooperative catalysis; however, examples of such processes are yet to be identified. Herein, we present such a method for creating different compounds with quaternary stereocenters by photoredox/Fe/chiral primary amine triple catalysis. This approach facilitates the connection of an unactivated alkyl source with a tertiary alkyl moiety, which is also rare. The scalable process exhibits mild conditions, does not necessitate the use of a base, and possesses a good functional-group tolerance. Preliminary investigations into the underlying mechanisms have provided valuable insights into the reaction pathway.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Li,

Zhang,

et al. 2024

J. Am. Chem. Soc.

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“…The optimal stereochemistry of the β-methyl group will be determined once again by the synthesis and evaluation of both diastereomers. A number of approaches to asymmetric synthesis of 2 have been published since the first report by Mukaiyama in 1980 [18], including the use of chiral auxiliary [19][20][21][22][23][24][25][26][27], chiral pool [28][29][30][31][32][33][34][35][36][37], other asymmetric syntheses [38][39][40] and catalytic asymmetric syntheses [41][42][43][44][45][46][47][48][49].…”

Section: Resultsmentioning

confidence: 99%

Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis

Breheny

Kingston

Doran

et al. 2021

IJMS

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Herein, we report antibacterial and antifungal evaluation of a series of previously prepared (+)-tanikolide analogues. One analogue, (4S,6S)-4-methyltanikolide, displayed promising anti-methicillin-resistant Staphylococcus aureus activity with a MIC of 12.5 µg/mL. Based on the antimicrobial properties of the structurally related (−)-malyngolide, two further analogues (4S,6S)-4-methylmalyngolide and (4R,6S)-4-methylmalyngolide bearing a shortened n-nonyl alkyl side chain were prepared in the present study using a ZrCl4-catalysed deprotection/cyclisation as the key step in their asymmetric synthesis. When these were tested for activity against anti-methicillin-resistant Staphylococcus aureus, the MIC increased to 50 µg/mL.

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N-Methoxy-N-methylacetamide

Harris

2001

Encyclopedia of Reagents for Organic Synthesis

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An asymmetric synthesis of (R)-(+)-2-nonyl-2-(carbomethoxy) cyclopentanone, a known precursor of the antibiotic (−)-malyngolide

Cited by 24 publications

References 11 publications

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis

N-Methoxy-N-methylacetamide

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