Total Synthesis of Amphirionin-4

Holmes, Michael; Kwon, Daniel; Taron, Matthew; Britton, Robert

doi:10.1021/acs.orglett.5b01844

Cited by 26 publications

(18 citation statements)

References 43 publications

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“…495) and ciguatoxin 54-deoxyCTX1B 496 have been achieved. 497,498 Polyketide synthesis genes unique to two Gambierdiscus species that produce maitotoxin 499 were characterised, perhaps implicating them in the biosynthesis of this metabolite. 500 Studies with Karenia brevis showed that brevetoxin 501 is localised in the chloroplasts and interacts with light harvesting complex II (LHCII) and thioredoxin, so is likely implicated in nonphotochemical quenching (NPQ).…”

Section: Dinoagellatesmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Dinoagellatesmentioning

confidence: 99%

Marine natural products

et al. 2017

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“…NHK coupling 16,17 between aldehyde 4 and vinyl iodide 22 in DMF at 0 °C to 23 °C for 24 h provided TBS protected amphirionin-4 as a major diastereomer in 60 % yield. The diastereoselectivity of this reaction was increased to (4:1) 13 in favor of the desired isomer 41 through strong 1,4-stereoinduction. Deprotection of the TBS-group with 70% HF, 30% pyridine in the presence of excess pyridine furnished (−)-amphirionin-4 ( 1 ) in excellent yield.…”

Section: Resultsmentioning

confidence: 98%

“…A similar strategy was also utilized by Britton and co-workers. 13 We planned to synthesize the vinyl iodide 3 from the corresponding allyl derivative through a Lewis acid catalyzed allylation of an oxocarbenium ion generated from α–hydroxy lactone 5 . This optically active lactone 5 could be readily obtained by the ozonolysis and subsequent reduction of commercially available α-methylene-γ-valerolactone 6.…”

Section: Resultsmentioning

confidence: 99%

“…Britton and co-workers reported the first total synthesis of (−)-amphirionin-4, corrected the sign of the specific rotation of the published data, and provided support for the structural assignment. 13 Subsequently, Kuwahara and co-workers reported their total synthesis of (−)-amphirionin-4 featuring a Sharpless kinetic resolution and iodoetherification as the key steps. 14 Our interest in (−)-amphirionin-4 arose from its potent activity against ST-2 cells and its unique structural features.…”

Section: Introductionmentioning

confidence: 99%

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Total syntheses of both enantiomers of amphirionin 4: A chemoenzymatic based strategy for functionalized tetrahydrofurans

Ghosh

Nyalapatla

2017

Tetrahedron

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The total syntheses of (−)-amphirionin-4 and (+)-amphirionin-4 have been achieved in a convergent and enantioselective manner. The tetrahydrofuranol cores of amphirionin-4 were constructed in optically active form by enzymatic resolution of racemic cis-3-hydroxy-5-methyldihydrofuran-2(3H)-one. The polyene side chain was efficiently synthesized using Stille coupling. The remote C8-stereocenter was constructed using the Nozaki-Hiyama-Kishi coupling reaction. A detailed 1H-NMR studies of Mosher esters of (−)-amphirionin-4 and (+)-amphirionin-4 were carried out to support the assignment of the absolute configurations of C-4 and C-8 asymmetric centers of amphirionin-4.

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“…The structure of (+)-amphirionin-4 was elucidated by Tsuda and co-workers using extensive NMR analysis and the absolute configuration of the C4 and C8 hydroxyl groups was determined by Mosher ester analysis . Recently, Britton and co-workers have reported the first synthesis of amphirionin-4 . However, the specific rotation of the synthetic compound was opposite to that reported for natural amphirionin-4. , Considering the extreme proliferation-promoting activity of (+)-amphirionin-4 in ST-2 cells, its structural features, and its potential medicinal application, we sought to develop a convergent and concise enantioselective synthesis of (+)-amphirionin-4.…”

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confidence: 99%

Enantioselective Total Synthesis of (+)-Amphirionin-4

Ghosh

Nyalapatla

2016

Org. Lett.

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An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically-active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective syn-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki-Hiyama-Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.

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Total Synthesis of Amphirionin-4

Cited by 26 publications

References 43 publications

Marine natural products

Marine natural products

Total syntheses of both enantiomers of amphirionin 4: A chemoenzymatic based strategy for functionalized tetrahydrofurans

Enantioselective Total Synthesis of (+)-Amphirionin-4

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