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.

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.

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 860-862 ◽  
Author(s):  
Yun Zhou ◽  
Chunxiao Liu ◽  
Lifeng Wang ◽  
Leng Han ◽  
Shicong Hou ◽  
...  
Keyword(s):  
Total Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Drugs ◽  
Asymmetric Catalytic ◽  
Cross Coupling Reaction ◽  
Tertiary Carbon ◽  
Key Steps

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

scholarly journals Synthesis of Piceatannol, an Oxygenated Analog of Resveratrol

2016 ◽  
Vol 11 (7) ◽  
pp. 1934578X1601100
Author(s):  
Takuya Tashiro ◽  
Shinobu Honzawa ◽  
Takumichi Sugihara
Keyword(s):  
Anticancer Activity ◽  
Red Wine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Beneficial Effects ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Trans Stilbene ◽  
Acid Catalyzed

Piceatannol (3,3′,4,5′-tetrahydroxy- trans-stilbene, 2), an oxygenated analog of resveratrol (1), was synthesized. It is one of the naturally occurring polyphenolic stilbenoids contained in red wine, and possesses many kinds of beneficial effects such as anticancer activity. The trans-stilbene skeleton of 2 was constructed by Pd-catalyzed Suzuki-Miyaura cross coupling reaction of triflate 8 with ( E)-alkenylboronoate 13. The key intermediate 13 was prepared diastereoselectively by acid-catalyzed hydroboration of pinacolborane 12 to alkyne 11.

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 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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