A new route to furanoeremophilane sesquiterpenoids. Synthesis of Senecio metabolites (±)-6-hydroxyeuryopsin, (±)-1,10-epoxy-6-hydroxyeuryopsin, (±)-toluccanolide A and (±)-toluccanolide C

Mace, Laura H.; Shanmugham, M. Sundaram; White, James D.; Drew, Michael G. B.

doi:10.1039/b513398j

Cited by 24 publications

(9 citation statements)

References 28 publications

(36 reference statements)

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“…To prove our working hypothesis, lithiated furan 22 was added to a solution of stemoamide ( 1 ) in THF at −78 °C (Scheme A). The nucleophilic addition of 22 proceeded with complete lactone selectivity.…”

Section: Resultsmentioning

confidence: 99%

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

et al. 2017

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A unified total synthesis of stemoamide-type alkaloids is reported. Our synthetic approach features the chemoselective convergent assembly of five-membered building blocks via stemoamide as the common precursor to tetracyclic natural products. The synthesis consists of two successive coupling reactions of the three five-membered building blocks. The first coupling reaction is the vinylogous Michael addition/reduction sequence, which enables the gram-scale synthesis of stemoamide. The second coupling reaction is a chemoselective nucleophilic addition to stemoamide. While the lactone-selective nucleophilic addition to stemoamide affords saxorumamide and isosaxorumamide, the lactam-selective reductive nucleophilic addition leads to the formation of stemonine. Both chemoselective nucleophilic additions enable direct modification of stemoamide, resulting in highly concise and efficient total syntheses of the stemoamide-type alkaloids.

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Section: Resultsmentioning

confidence: 99%

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

et al. 2017

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“…340,341 (−)-Carvone has been used as starting material in a synthesis of (−)-aristolochene, 342 whilst a racemic synthesis of 6hydroxyeuryopsin, 1,10-epoxy-6-hydroxyeuryopsin, toluccanolide A and toluccanolide C has been reported. 343 The structures of several compounds produced in the basic hydrolysis of four eremophilane esters, which were isolated from Robinsonecio gerberifolius, have been assigned. 344 A synthesis of (±)-bakkenolide A has been described, 345 whilst an approach to the diastereoselective construction of the norbakkane skeleton has been reported.…”

Section: Eremophilane and Bakkanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2010

Nat. Prod. Rep.

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“…A literature survey revealed that 3-iodofurans [6a, 17] and 3-(hydroxymethyl)furans [18] are two very useful classes of furan-based building block. Keeping the synthetic importance of these two furan classes in mind, we decided to prepare 3-iodo-and 3-hydroxymethylsubstituted 2,3-dideoxy-hex-2-enopyranosides and to convert them into the corresponding 3-iodo-and 3-hydroxymethyl-substituted furan derivatives by using the synthetic strategy described above.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Enantiomerically Pure 2‐ and 2,3‐Disubstituted Furans Catalysed by Mixed Lewis Acids: An Easy Route to 3‐Iodofurans and 3‐(Hydroxymethyl)furans

Saquib¹,

Husain²,

Kumar³

et al. 2009

Chemistry A European J

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Simple and efficient syntheses, catalysed by a mixed Lewis acid system (ZrCl(4)/ZnI(2)), of enantiomerically pure 2- and 2,3-disubstituted furan derivatives--including important synthons such as 3-iodofuran and 3-(hydroxymethyl)furan derivatives--from commercially available 3,4,6-tri-O-acetyl-D-glucal are described. The transformation is achieved through a synergistic interaction between ZrCl(4) and ZnI(2) in catalytic amounts.

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A new route to furanoeremophilane sesquiterpenoids. Synthesis of Senecio metabolites (±)-6-hydroxyeuryopsin, (±)-1,10-epoxy-6-hydroxyeuryopsin, (±)-toluccanolide A and (±)-toluccanolide C

Cited by 24 publications

References 28 publications

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

Natural sesquiterpenoids

Facile Synthesis of Enantiomerically Pure 2‐ and 2,3‐Disubstituted Furans Catalysed by Mixed Lewis Acids: An Easy Route to 3‐Iodofurans and 3‐(Hydroxymethyl)furans

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