Jasisoquinolines A and B, Architecturally New Isoquinolines, from a Marine Sponge <i>Jaspis</i> sp.

Imae, Yasufumi; Takada, Kentaro; Murayama, Shuhei; Okada, Shigeru; Ise, Yuji; Matsunaga, Shigeki

doi:10.1021/ol201823w

Cited by 9 publications

(4 citation statements)

References 21 publications

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“…The ROESY correlations of H-5/H-8 β , H-7/H-8 α , Me-12/H-5, Me-15/H-6, and H-6/H-1 indicated the α -orientations of H-1, H-6, and H-7 and the β -orientations of H-4 and H-5. The absolute configuration was determined by application of the Snatzke’s helicity rule1013141516. The P/M -helicity of the dihydropyran ring in FPMs controlled the signs of Cotton effects approximately between 270–310 nm (Fig.…”

Section: Resultsmentioning

confidence: 99%

New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta

Shang

Yang

Liu

et al. 2016

Sci Rep

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Seven new formyl phloroglucinol meroterpenoids (FPMs), namely eucalrobusones J-P (1–7), as well as three known ones (8–10) were isolated from the leaves of Eucalyptus robusta. Their structures were elucidated by spectroscopic data analysis, and their absolute configurations were determined by applications of the Snatzke’s helicity rule and the electron circular dichroism (ECD) calculation. These FPMs are diverse in coupling patterns between phloroglucinol and sesquiterpenoid units, forming novel polycyclic ring systems. Compound 1 possesses a new carbon skeleton that a 1-oxaspiro[5.6]dodecane core is formed through C-14 rather than C-4 of the aromadendrane moiety. Compound 2 features a novel 6/7/5 ring-fused 6-oxabicyclo[3.2.2]nonane skeleton. Compounds 3–5 are rare aristolane-based FPMs. By forming different oxo bridges, compound 3 is the first sample of FPM with benzo-dihydrofuran structure, and compound 4 possesses a novel 6/6/6/6/3-fused pentacyclic skeleton. Compounds 1, 6, and 8 exhibited significant antifungal activities against Candida glabrata with MIC50 values of 2.57, 1.95, and 2.49 μg/mL, respectively.

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Section: Resultsmentioning

confidence: 99%

New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta

Shang

Yang

Liu

et al. 2016

Sci Rep

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“…The closely related jasisoquinoline B (136) was studied in the same manner and proven to be the 27-demethyl analogue of 135 (Scheme 26). 53 Joint Application with Other Reactions. The combined use of this reaction with other chemical transformations was also effective.…”

Section: ■ Ozonolysismentioning

confidence: 99%

Application of Oxidative and Reductive Transformations in the Structure Determination of Marine Natural Products

2020

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“…Various reliable methods involving asymmetric synthesis have been reported to date . 1,2,3,4‐Tetrahydroisoquinoline‐1‐carboxylic acid and its derivatives are of particular interest as potential building blocks for modified peptides or other pharmacologically active compounds . Such derivatives have been produced via Ugi‐type reactions, which have also been applied to the synthesis of medicinally relevant heterocycles, although the practical applications of this approach remain limited.…”

Section: Chlorosilane‐promoted Addition Reaction Of Isocyanides To 3mentioning

confidence: 99%

Carboxylic Acid Free Novel Isocyanide‐Based Reactions

Soeta

Ukaji

2014

The Chemical Record

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In order to develop a practical method for the construction of drug-like and heterocyclic compounds, we have designed a novel Passerini- or Ugi-type reaction system where a compound (which we write in the general form as Z-X) composed of an electrophilic (Z) and a nucleophilic group (X) could essentially perform the same function as the carboxylic acid. Based on this concept, we have developed the O-silylative Passerini reaction and the borinic acid catalyzed α-addition of isocyanides to aldehydes and water. In addition, we have designed and demonstrated the addition reaction of isocyanides to nitrones in the presence of TMSCl to afford the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxyamides. Furthermore, a novel [5 + 1] cycloaddition of isocyanide was explored with C,N-cyclic N'-acyl azomethine imines as a "1,5-dipole" via a strategy involving intramolecular trapping of the isocyanide.

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Jasisoquinolines A and B, Architecturally New Isoquinolines, from a Marine Sponge Jaspis sp.

Cited by 9 publications

References 21 publications

New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta

New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta

Application of Oxidative and Reductive Transformations in the Structure Determination of Marine Natural Products

Carboxylic Acid Free Novel Isocyanide‐Based Reactions

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