Abstract:An efficient synthesis of propolisbenzofuran B, which possesses promising anticancer activity, is reported. The key cyclohexanone framework of this tricyclic natural product has been constructed employing a Rh-catalyzed intramolecular olefin hydroacylation. The requisite key olefin intermediate was synthesized by using gold-catalyzed allenyl ether [1,3] O → C rearrangement.
“…Among these two chemical compounds, the unrivaled tricyclic core skeleton in propolisbenzofuran B and its biological activity is topic of main interest for organic chemists and biologists.Fig. 1Propolisbenzofuran A (left) and B (right) [14].…”
Section: Introductionmentioning
confidence: 99%
“…Srinivas et al. reported the total synthesis of propolisbenzofuran B via Rh-catalyzed intramolecular olefin hydroacylation [14]. At their synthesis approach, the olefin intermediate was synthesized by using gold-catalyzed allenyl ether [1, 3] O→C rearrangement.…”
This investigation deals with some structural and spectroscopic aspects of propolisbenzofuran B molecule as one of the most important bioactive molecules which exists in the bee propolis composition. FT-IR vibrational analysis carried-out at B3LYP/6–311++G(d,p) level of the theory. 1H and 13C NMR chemical shift have been predicted with GIAO method. TD- DFT calculations have been established to predict the UV- Vis spectral analysis for propolisbenzofuran B molecule. The detailed structural analysis such as electronic characterization, HOMO and LUMO, DOS plot, Molecular Electronic Potential (MEP), Natural Bond Orbital (NBO) are performed and discussed for studied molecule.
“…Among these two chemical compounds, the unrivaled tricyclic core skeleton in propolisbenzofuran B and its biological activity is topic of main interest for organic chemists and biologists.Fig. 1Propolisbenzofuran A (left) and B (right) [14].…”
Section: Introductionmentioning
confidence: 99%
“…Srinivas et al. reported the total synthesis of propolisbenzofuran B via Rh-catalyzed intramolecular olefin hydroacylation [14]. At their synthesis approach, the olefin intermediate was synthesized by using gold-catalyzed allenyl ether [1, 3] O→C rearrangement.…”
This investigation deals with some structural and spectroscopic aspects of propolisbenzofuran B molecule as one of the most important bioactive molecules which exists in the bee propolis composition. FT-IR vibrational analysis carried-out at B3LYP/6–311++G(d,p) level of the theory. 1H and 13C NMR chemical shift have been predicted with GIAO method. TD- DFT calculations have been established to predict the UV- Vis spectral analysis for propolisbenzofuran B molecule. The detailed structural analysis such as electronic characterization, HOMO and LUMO, DOS plot, Molecular Electronic Potential (MEP), Natural Bond Orbital (NBO) are performed and discussed for studied molecule.
“…Benzofuran is a heterocyclic compound in which benzene and furan are fused together. The compounds containing the benzofuran skeleton has diverse biological activities such as antifungal [1], anti-microbial [2], anticancer [3,4], calcium entry blockers [5] and many other biological functions. Aroyl-benzofurans are important class of benzofuran derivatives which constitutes the structural moiety of natural products and pharmaceutical drugs.…”
Aroyl-benzofurans are important heterocyclic compounds which displayed a wide range of biological activities and important structural motif of many pharmaceutical drugs. Most of the pharmaceutical drugs containing the aroyl-benzofuran structural core have severe side effects which limits its usage. Some of the drugs containing the aroyl-benzofuran structural core were withdrawn from the market due to its toxicity. So, there is a need for the development of new synthetic methods to functionalize these molecules which play a significant role in drug discovery program. The current review focuses on the C-H functionalization of 2-/3-aroyl-benzofurans which includes alkylation, arylation, phosphonylation and benzoylation which plays a crucial role in developing new anti-arrhythmic drugs.
“…2 The unique structural features having a 1-aryl-2,3-dihydrodibenzo[ b,d ]furan-4(1 H )-one unit along with its bioactivities fascinated organic chemists for its total synthesis. 3 The Thomson group reported the first total synthesis of racemic compound (±)- 1 in 17 steps with an overall yield of 2.85% (8.29% based on the recovery of starting material), where the 1-aryl-2,3-benzofuranone core was constructed at a late stage by utilizing aromatizing annulation reaction of a meticulously designed 1,4-diketone (1,1′-dicyclohexenone) with pre-built substitutions. 3 a Later in 2017, Ramana et al also synthesized racemic 1 in 16 steps with poor selectivity with an overall yield of only 1.05% (3.6% based on the recovery of starting material), where the 3,5,6 trisubstituted benzofuran intermediate was built in an early stage along with an equal amount of the 3,5,7-trisubstituted regioisomer.…”
mentioning
confidence: 99%
“…The synthesized compound 1 displayed identical spectral data and optical rotation to that reported for the natural product. 2 a ,3…”
The first asymmetric total synthesis of (+)-propolisbenzofuran B is accomplished in 11 steps with an overall yield of 11.9%. The key steps are tandem deacetylative Sonogashira coupling-annulation reaction to synthesize...
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