The Marine Bromotyrosine Derivatives

Peng, Jiangnan; Jing, Li; Hamann, Mark T.

doi:10.1016/s1099-4831(05)61002-4

Cited by 79 publications

(108 citation statements)

References 274 publications

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“…Synthesis of Lamellarins D (35), L (15), and N (40) a a Reagents and conditions: (i) 97 or 98 (1.0 equiv), Pd(PPh 3 ) 4 (2 mol %), THF, reflux, 4 h (99, 76%; 100, 77%); (ii) (1)101 (2.0 equiv), Pd(PPh 3 ) 4 (8 mol %), THF, reflux, 18 h, (2) concd HCl, MeOH, reflux 1 h (102, 98%; 103, 95%); (iii) (1) 40% KOH-EtOH (1/1), reflux, 3 h, (2) cat. p-TsOH, CH 2 Cl 2 , reflux, 1 h (104, 90%; 105, 91%); (iv) Cu 2 O, quinoline, 220 °C, 7 min (106, 94%; 107, 99%); (v) …”

Section: Methodsmentioning

confidence: 99%

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

et al. 2007

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Section: Methodsmentioning

confidence: 99%

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

et al. 2007

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“…1 More than 30 such bromotyrosine derivatives, named psammaplysins A−Y or ceratinamides A and B, have been described, 2−12 with reports of significant toxicity to cancer cell lines, 4−6,12 antibacterial 2,6 or anti-HIV activity, 5 and antifouling activity against barnacle larvae. 6 Psammaplysins I and J were reported without any bioassay data.…”

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confidence: 99%

Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine SpongeAplysinella strongylata

et al. 2015

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The absolute configuration of psammaplysin A (1) has been assigned as (6R,7R) using experimental and calculated electronic circular dichroism (ECD) data and NMR analysis of MPA esters prepared from the acetamide derivative of 1. Detailed conformational analyses of a truncated model compound of 1 with an in vacuo method and with the PCM solvent model for MeOH have identified the major conformers and factors governing the ECD spectrum of 1. The correlation of the ECD data with the stereochemistry of 1 allows configurational assignment of related psammaplysin analogues on the basis of their ECD spectra.

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“…The established role of 2-isoxazolines as valuable intermediates in organic synthesis is attributed to their capacity to mask other functionalities within a stable form that allows further substitution of the ring [20]. α,β-Unsaturated ketones [21], β-hydroxycarbonyl compounds [22], and 1,3-aminoalcohols [23] are the most important structural units available from 2-isoxazolines by reductive cleavage of the hetero ring.…”

Section: Introductionmentioning

confidence: 99%

“…α,β-Unsaturated ketones [21], β-hydroxycarbonyl compounds [22], and 1,3-aminoalcohols [23] are the most important structural units available from 2-isoxazolines by reductive cleavage of the hetero ring. Although the isoxazoline building block appears to be a rare functionality both in secondary metabolites found in nature [20,24] and among marketed pharmaceutical agents [25], several synthetic derivatives have been reported to exhibit valuable biological activities [25,26]. Several methods have been devised to construct such bio-important compounds, where the 1,3-dipolar cycloaddition of nitrile oxides to an unsaturated substrate has been widely investigated [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel steroidal 16-spiroisoxazolines by 1,3-dipolar cycloaddition, and an evaluation of their antiproliferative activities in vitro

et al. 2014

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Efficient synthesis of novel 16-spiroisoxazolines in the androst-5-ene series was carried out by 1,3-dipolar cycloadditions of different aryl nitrile oxides to 3β-acetoxy-16-methylene-androst-5-en-17-one. During the intermolecular ring closures, the attack of the O terminus of the nitrile oxide dipole from the α side on C-16 predominated for steric reasons permitting the reactions to occur in a regio-and stereoselective manner. The minor isomers in which the angular methyl group on C-13 and the O atom of the isoxazoline heteroring were in the β, β-cis orientation were obtained in a yield of only ∼10 %. Moreover, the conversions were influenced to a certain extent by the substituents on the aromatic moiety of the 1,3-dipoles. The stereostructures of the related diastereomers were confirmed by 2D NMR methods. Deacetylation of the primarily formed main products resulted in the corresponding 3β-OH analogs, which were further reduced to furnish 3β, 17β-diols. All of the synthetized compounds were subjected to in vitro pharmacological studies in order to investigate their antiproliferative

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The Marine Bromotyrosine Derivatives

Cited by 79 publications

References 274 publications

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine SpongeAplysinella strongylata

Synthesis of novel steroidal 16-spiroisoxazolines by 1,3-dipolar cycloaddition, and an evaluation of their antiproliferative activities in vitro

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