Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1561-1575 ◽  
Author(s):  
Faiz Ahmed Khan ◽  
Mulla Althafh Hussain
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aldol Condensation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Account ◽  
Curcumin Analogues ◽  
Cross Coupling Reaction ◽  
Sigmatropic Shift ◽  
Novel Approaches

A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.

Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate

2012 ◽  
Vol 2012 (26) ◽  
pp. 5018-5027 ◽  
Author(s):  
Takumi Abe ◽  
Toshiaki Ikeda ◽  
Tominari Choshi ◽  
Satoshi Hibino ◽  
Noriyuki Hatae ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Tandem Cyclization

scholarly journals Total synthesis of elansolids B1 and B2

2017 ◽  
Vol 13 ◽  
pp. 1280-1287 ◽  
Author(s):  
Liang-Liang Wang ◽  
Andreas Kirschning
Keyword(s):  
Antibacterial Activity ◽  
Secondary Metabolites ◽  
Total Synthesis ◽  
Second Generation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Gram Positive Bacteria ◽  
Cross Coupling Reaction ◽  
Gliding Bacterium ◽  
Coupling Sequence

The elansolids A1–A3, B1, and B2 are secondary metabolites formed by the gliding bacterium Chitinophaga sancti. They show antibacterial activity against Gram-positive bacteria. A second generation total synthesis of the antibiotic elansolid B1 (2) and the first synthesis of elansolid B2 (3) are reported. In contrast to previous work, the (Z,E,Z)-triene at C10–C15 was assembled by using an optimized C–C cross-coupling sequence with a Suzuki cross-coupling reaction as key step.

scholarly journals Total Synthesis of Surinamensinols A and B

SynOpen ◽  
2020 ◽  
Vol 04 (04) ◽  
pp. 84-88
Author(s):  
Ahmed Al-Harrasi ◽  
Satya Kumar Avula ◽  
Biswanath Das ◽  
Rene Csuk ◽  
Ahmed Al-Rawahi
Keyword(s):  
Total Synthesis ◽  
Allyl Alcohol ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ethyl Lactate ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Synthetic Sequence ◽  
Key Steps ◽  
Single Approach

AbstractAn efficient total synthesis of the naturally occurring anti-inflammatory and antitumour 8-O-4′-neolignans, surinamensinols A and B, has been accomplished from commercially available allyl alcohol and (S)-ethyl lactate. The synthetic sequence involves a palladium-catalysed Suzuki–Miyaura cross-coupling reaction followed by a chiral Mitsunobu­ reaction as the key steps. This is the first report of the simultaneous stereoselective total synthesis of surinamensinols A and B through a single approach involving only six steps.

scholarly journals Total Synthesis of the Anti-inflammatory and Pro-resolving Lipid Mediator MaR1n−3 DPAUtilizing an sp3-sp3Negishi Cross-Coupling Reaction

2014 ◽  
Vol 20 (45) ◽  
pp. 14575-14578 ◽  
Author(s):  
Jørn Eivind Tungen ◽  
Marius Aursnes ◽  
Jesmond Dalli ◽  
Hildur Arnardottir ◽  
Charles Nicholas Serhan ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Lipid Mediator ◽  
Cross Coupling Reaction ◽  
Anti Inflammatory

Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L.

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4253-4262
Author(s):  
Abel A. Arroyo Aguilar ◽  
Gabriela N. Ledesma ◽  
Bárbara Tirloni ◽  
Teodoro S. Kaufman ◽  
Enrique L. Larghi
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Nitro Group ◽  
Nmr Spectra ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Agreement ◽  
Nitrobenzoic Acid ◽  
Microwave Assisted ◽  
Cross Coupling Reaction

The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki–Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1H NMR spectra of the synthetic and natural product were in full agreement.

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