Synthesis of Highly Functionalized Hydrindanes via Sequential Organocatalytic Michael/Mukaiyama Aldol Addition and Telescoped Hydrozirconation/Cross-Coupling as Key Steps: En Route to the AB System of Clifednamides

2021 ◽  
Author(s):  
Moritz Sinast ◽  
Birgit Claasen ◽  
Yannick Stöckl ◽  
Andreas Greulich ◽  
Anna Zens ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mukaiyama Aldol ◽  
Aldol Addition ◽  
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.

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

Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

2018 ◽  
Vol 54 (4) ◽  
pp. 374-377 ◽  
Author(s):  
Takahiro Kawajiri ◽  
Reiya Ohta ◽  
Hiromichi Fujioka ◽  
Hironao Sajiki ◽  
Yoshinari Sawama
Keyword(s):  
Aromatic Aldehyde ◽  
Aldol Reaction ◽  
Aliphatic Aldehydes ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Aldol Addition

Unprecedented chemoselectivity between aromatic and aliphatic aldehydes has been achieved in the Mukaiyama aldol reaction using aldehyde-derived silyl enol ethers.

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.

ChemInform Abstract: A Rapid Injection NMR Study of the Chelation Controlled Mukaiyama Aldol Addition: TiCl4 versus LiClO4 as the Lewis Acid.

ChemInform ◽  
2010 ◽  
Vol 23 (43) ◽  
pp. no-no
Author(s):  
M. T. REETZ ◽  
B. RAGUSE ◽  
C. F. MARTH ◽  
H. M. HUEGEL ◽  
T. BACH ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Nmr Study ◽  
Rapid Injection ◽  
Mukaiyama Aldol ◽  
Aldol Addition

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.

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