Synthesis of Biaryl Derivatives by Using Ruthenium-Mediated [2+2+2] Cyclotrimerization and Suzuki-Miyaura Cross-Coupling as Key Steps

Synthesis ◽  
2011 ◽  
Vol 2011 (10) ◽  
pp. 1581-1586 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Vittal Seema ◽  
Shaikh Mobin
Keyword(s):  
Cross Coupling ◽  
Key Steps

A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

2019 ◽  
Vol 16 (12) ◽  
pp. 931-934 ◽  
Author(s):  
Alexandra Kamlah ◽  
Franz Bracher
Keyword(s):  
Pyridine Ring ◽  
Cross Coupling ◽  
Antirrhinum Majus ◽  
New Synthesis ◽  
Short Synthesis ◽  
Regioselective Oxidation ◽  
Key Steps

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

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 An enantioselective synthesis of the C24–C40 fragment of (−)-pulvomycin

2014 ◽  
Vol 50 (38) ◽  
pp. 4901-4903 ◽  
Author(s):  
Sandra Börding ◽  
Thorsten Bach
Keyword(s):  
Synthesis Method ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Diastereoselective Addition ◽  
Key Steps

The C24–C40 fragment of (−)-pulvomycin was prepared in enantiomerically pure form using a concise synthesis method (15 linear steps from d-fucose, 6.8% overall yield) featuring a diastereoselective addition to an aldehyde, a β-selective glycosylation and a Stille cross-coupling as the key steps.

Synthesis of fully functionalized aglycone of lycoperdinoside A and B

2015 ◽  
Vol 13 (1) ◽  
pp. 115-124 ◽  
Author(s):  
Balla Chandrasekhar ◽  
Sudhakar Athe ◽  
P. Purushotham Reddy ◽  
Subhash Ghosh
Keyword(s):  
Cross Coupling ◽  
Aldol Reactions ◽  
Key Steps

Synthesis of fully functionalized aglycone of lycoperdinoside A and B is achieved via Pd-catalyzed Stille–Migita cross coupling and Evans syn- and anti aldol reactions as key steps.

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 Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

2018 ◽  
Vol 14 ◽  
pp. 2468-2481 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Milind Meshram ◽  
Chandravathi Chakkapalli
Keyword(s):  
Recent Work ◽  
Claisen Rearrangement ◽  
Cross Coupling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enyne Metathesis ◽  
Cross Metathesis ◽  
Diels Alder Reaction ◽  
Synergistic Approach ◽  
Key Steps

This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of complex targets and fulfill synthetic brevity.

scholarly journals Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

2019 ◽  
Vol 15 ◽  
pp. 761-768 ◽  
Author(s):  
Iteng Ng-Choi ◽  
Àngel Oliveras ◽  
Lidia Feliu ◽  
Marta Planas
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Cross Coupling ◽  
Phase Synthesis ◽  
Microwave Assisted ◽  
Bicyclic Compounds ◽  
Key Steps

A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides.

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