2013
DOI: 10.1002/ange.201303334
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Total Synthesis of Indotertine A and Drimentines A, F, and G

Abstract: Eine radikalische intermolekulare konjugierte Addition führte in den ersten Totalsynthesen der abgebildeten Naturstoffe zu den Pyrroloindolin‐Alkaloiden der Drimentin‐Familie. Durch eine Iminium‐Olefin‐Cyclisierung nach biologischem Vorbild konnte Drimentin F weiter in Indotertin A umgewandelt werden.

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Cited by 39 publications
(16 citation statements)
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“…Notably, 31 and 32 were inert under the mild acidic conditions described above. This reaction is similar to the bioinspired transformation from drimentine F into indotertine A reported by us previously, [11] in which the postulated cationic intermediate undergoes a regiospecific proton elimination to form the trisubstituted C=C bond. We then repeated the oxidation/cyclization sequence from 21 and prolonged the times of acid treatment.…”
supporting
confidence: 85%
See 1 more Smart Citation
“…Notably, 31 and 32 were inert under the mild acidic conditions described above. This reaction is similar to the bioinspired transformation from drimentine F into indotertine A reported by us previously, [11] in which the postulated cationic intermediate undergoes a regiospecific proton elimination to form the trisubstituted C=C bond. We then repeated the oxidation/cyclization sequence from 21 and prolonged the times of acid treatment.…”
supporting
confidence: 85%
“…It is noteworthy that a similar aza-Prins reaction was observed during our synthesis of indotertine A. [11] A Friedel-Crafts annulation and subsequent retro Friedel-Crafts fragmentation would then deliver 1, presumably through the intermediacy of the dearomatized 7. The driving force of this cascade may be attributable to the steric proximity of the positive charges and the electron-rich functionalities, as well as the re-aromatization of 7.…”
supporting
confidence: 65%
“…Two emission bands could be observed for these five samples. The emission at around 380-400 nm is the characteristic near-band-edge emission due to the recombination of free photogenerated electrons and holes [44] and the other one is a deep-level emission mostly in the green region (471 nm), which is produced by the transition of excited optical centers from the deep level to the valence level, such deep-level emission being usually accompanied by the presence of structural defects [19,45]. The red-shift of UV emission was observed from 390 to 412 nm due to the increase in size of the particles [46,47].…”
Section: Photoluminescence Of Zno Nanostructuresmentioning
confidence: 99%
“…[39] Examples of oxidation and olefination were reported with ester and ketone as directing group but in both cases a mixture of C2-and C8-functionalized products were obtained (Scheme 21.b,c). [40,41] Despite one example of halogenations reported in 2013, [42] carbonyl-directed C8-functionalization is quite rare in the literature. In 2016, Xia and Fu's team developed a palladiumcatalyzed C8-triflation of naphthalenes (Scheme 22).…”
Section: -Carbonylnaphthalene Derivatives In C8-functionalizationmentioning
confidence: 99%