<b>Synthesis of Olivacine</b>

Wenkert, Ernest; Dave, K. G.

doi:10.1021/ja00860a022

Cited by 30 publications

(22 citation statements)

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“…The required compounds 5, 6, 7 and 8 were prepared from ethyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetate 1 (Scheme I) [26]. Synthesis of thioketal 2 was achieved under mild condition by refluxing of 1 for 20 h in chloroform using 1,2-ethanedithiol and zinc triflate as a catalyst [27].…”

Section: Resultsmentioning

confidence: 99%

Studies on the synthesis of the azocino[4,3‐b]indole framework and related compounds

Uludag

Patir

2007

Journal of Heterocyclic Chem

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An efficient method for the synthesis of C-4 position alkylated azocino [4,3-b]indole 13 and 18 is described. Reduction of compounds 5, 6, 7 and 8 yielded the corresponding alcohols. Compounds 5, 6, 7 and 8 were synthesized through several steps starting from 1. The resulting alcohols underwent acid catalyzed ring closure to give tetracyclic azocino [4,3-b]indole 9, 10, 11 and 12. Finally, compounds 9 and 17 were alkylated at C-4 position to the corresponding products 13 and 18. The structure of the compounds 13 and 18 has been confirmed by X-ray single crystal analysis.

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Section: Resultsmentioning

confidence: 99%

Studies on the synthesis of the azocino[4,3‐b]indole framework and related compounds

Uludag

Patir

2007

Journal of Heterocyclic Chem

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“…[1] Later his postulation was confirmed by experimentale vidence of feeding radioactive-labelledf orms of secodine and 17,18-dihydrosecodine-17-ol to various alkaloid-bearing plants ( Figure 1). [2] Inspired by the biogenesis of such alkaloids,m any research groups adopted biomimetic strategies involving aD iels-Alder reactiono fs ecodine analogs with an in-situ generated or preformed acrylate moiety for their synthesis.…”

Section: Introductionmentioning

confidence: 90%

Expedient Introduction of β‐Methoxyacrylate Unit onto 3‐Substituted Indoles and Application of the Resulting Indole‐Dienes in Organocascade toward Indolino‐Polycyclics

Guo

Huang

et al. 2015

Adv Synth Catal

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An efficient methodology for introducing a b-alkoxy acrylate unit onto the indolic C-2 position of 3-substituted indolesh as been realized by oxidative radical alkylation of indoles with ax anthate bearing dialkyl acetal functionality and subsequent elimination of alcohol by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene( DBU). Thei ndole-dienes thus prepared are quite stablea nd can be stored at room temperature for several months without obvious deterioration. Next,t he indole-dienesw ere successfullya pplied in an asymmetric cascade reaction with propargyl aldehyde catalyzed by MacMillans imidazolidinone and trichloroacetic acid (TCA), affording tetracyclic spiroindolines or tricyclic hydrocarbazoles in good to excellent yields with excellent ees. Thep racticality of this cascade was demonstrated by ag ram scale preparation of at etracyclic spiroindoline product with as low as 1mol% catalyst loadinga nd further elaboration of this spiroindoline compound into valuable intermediates for alkaloid synthesis.

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“…Pyridocarbazole alkaloids such as olivacine and ellipticine are some of the most potent drugs for the treatment of a variety of cancers. Thus a number of methods have been developed for the synthesis of ellipticine and its analogues (Pelletier, 1970), including the use of the non-protected ethyl 2-(1-oxo-2,3,4,9tetrahydro-1H-carbazole-2-yl)acetate derivative of the title compound, (I), as the starting material (Wenkert & Dave, 1962). Furthermore, after transformation of the title compound into 4-oxo-tetrahydrocarbazole derivatives, useful intermediates for the synthesis of the azocino[4.3-b]indole system may be obtained (Magnus et al, 1992).…”

Section: Commentmentioning

confidence: 99%