Syntheses of bis(indolyl)-piperazine alkaloids, dragmacidin B and C, and dihydrohamacanthin A

Kawasaki, Tomomi; Ohno, Kohsuke; Enoki, Hidetaka; Umemoto, Yasuko; Sakamoto, Masanori

doi:10.1016/s0040-4039(02)00771-2

Cited by 33 publications

(8 citation statements)

References 14 publications

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“…α‐(3‐Indolyl)glycines ( 86 ; R 1 : H, R 2 : CO 2 R) are an important family of synthetic intermediates for the preparation of nonproteinogenic amino acids 97c,d,f. Indolylglycines can be conveniently obtained as a racemic mixture by spontaneous98, 99a,b or catalyzed99c Friedel–Crafts alkylation of indoles with preformed or in situ prepared glyoxylate imines.…”

Section: Reaction With Cx Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

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Section: Reaction With Cx Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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“…247 Two depsipeptides with nematocidal activity, phoriospongins A 269 and B 270, were isolated from both a Phoriospongia species and Callyspongia bilamellata from southern Australia. 297 The trans isomer of dihydrohamacanthin A from the same sponge was also synthesised along with the cis isomer of dragmacidin C. 298 Dragmacidin D, isolated from a Spongosorites species, 299,300 has been synthesised as a racemic mixture. 249 The determination of the presence of (R)-allo-threonine and (R)-alanine in their structures by use of Marfey's reagent led to the re-examination of the stereochemistry of callipeltin A 273, originally isolated from a Callipelta species.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2004

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This review covers the literature published in 2002 for marine natural products, with 579 citations (413 for the period January to December 2002) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds (677 for 2002), together with their relevant biological activities, source organisms and country of origin. Syntheses that lead to the revision of structures or stereochemistries have been included (114), including any first total syntheses of a marine natural product.

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“…The condensation of the obtained acid and indolylglycine using BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) and DIEA (N,N-diisopropylethylamine) proceeded diastereoselectively to give dipeptides (two diastereomers in 58% and 40% yields). Successive treatment of the appropriate diastereomer with HCO 2 H and with NH 3 led to the deprotection and cyclization, and the final product dragmacidin C was obtained in the last reduction step with borane in 42% yield (Kawasaki et al, 2002). The synthesis of didenmolines A (4) and C (5) enabled the unambiguous confirmation of the proposed structures and provided sufficient material for biological testing (Schumacher and Davidson, 1995) (Fig.…”

Section: Total Synthesis Of Brominated Secondary Metabolitesmentioning

confidence: 90%

Ascidian halogen-containing secondary metabolites from the family didemnidae

Djordjevic

Radulović

2019

Facta Univ Phys Chem Technol

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This review summarizes current knowledge concerning the isolation, structural elucidation, biological/pharmacological activities, and total synthesis of halogen-containing secondary metabolites isolated from ascidians of the family Didemnidae. Overall, 81 compounds are presented, displaying great structural diversity and possessing a number of significant biological/pharmacological properties. In addition to the most numerous brominated compounds, chlorinated and iodinated ones were also found. The most prolific genus in regard to the number of published papers and isolated molecules is the genus Didemnum, which was treated separately from the rest of the genera of the ascidian family. The structural complexity of the isolated metabolites prompted a number of synthetic endeavors that not only provided conclusive proof of the structure of the metabolites but also enabled the biological tests and the possible application of these metabolites.

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Syntheses of bis(indolyl)-piperazine alkaloids, dragmacidin B and C, and dihydrohamacanthin A

Cited by 33 publications

References 14 publications

Catalytic Functionalization of Indoles in a New Dimension

Catalytic Functionalization of Indoles in a New Dimension

Marine natural products

Ascidian halogen-containing secondary metabolites from the family didemnidae

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