New route to (−)-frontalin and (−)-malyngolide via epoxyketone rearrangement

Asaoka, Morio; Hayashibe, S.; Sonoda, S.; Takei, Hisashi

doi:10.1016/s0040-4020(01)96151-4

Cited by 32 publications

(8 citation statements)

References 13 publications

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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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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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“…The isomerization of the cyclic a,b-epoxyketone 18 into 1,3-dicarbonyl compound 19 was the key stage in the synthesis of an insect pheromone ()-frontaline 20 and of the naturally occurring antibiotic ()-malyngolide 21 found in sea organisms [23] (Scheme 7).…”

Section: Intramolecular Transformations Of Epoxycarbonyl Compounds Ismentioning

confidence: 99%

Intramolecular Involvement of an Oxygen-containing Nucleophilic Group in Epoxy Ring Opening

2005

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“…491 Two new ciguatoxins, CTX-2 and CTX-3, have been isolated from the moray eel Lycodontis javanicus but the structures were not completely characterized. 49…”

Section: Tunicatesmentioning

confidence: 99%