Stereoselective synthesis of tetrazole CB92834, a potent retinoid compound

Garipova, Goulnara; Gautier, Arnaud; Piettre, Serge R.

doi:10.1016/j.tet.2005.03.023

Cited by 20 publications

(13 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The open-chain intermediate 24 than cyclizes to the 1-[dimethyl(trimethylsilyloxy)stannyl]-5-ST 25 (Scheme 19). [88] Scheme 20. [84] The catalytic complex 23 is then regenerated through the simple S N 2 reaction between 25 and TMSN 3 via transition state 26 (Scheme 20).…”

Section: Methods Using Organometallic and Organosilicon Azidesmentioning

confidence: 99%

Synthesis and Functionalization of 5‐Substituted Tetrazoles

2012

View full text Add to dashboard Cite

Tetrazoles are synthetic heterocycles with numerous applications in organic chemistry, coordination chemistry, the photographic industry, explosives, and, in particular, medicinal chemistry. In organic chemistry, 5‐substituted tetrazoles are used as advantageous intermediates in the synthesis of other heterocycles and as activators in oligonucleotide synthesis. In drug design, 5‐monosubstituted tetrazoles are the most important tetrazole derivatives because they represent non‐classical bioisosteres of carboxylic acids, with similar acidities but higher lipophilicities and metabolic resistance. In this review we focus on the preparation and further functionalization of these heterocycles. Firstly, the role of 5‐substituted tetrazoles in medicinal chemistry is described, including examples of their effects on pharmacokinetics, pharmacodynamics, and metabolism of the associated drugs. Then, the main synthetic approaches to 5‐substituted tetrazoles – consisting of methods based on acidic media/proton catalysis, Lewis acids, and organometallic or organosilicon azides – are presented, from the early procedures to the most recent ones, with special attention paid to the reaction mechanisms. Functionalization of 5‐substituted tetrazoles is a challenging task because it usually leads to the formation of two isomers, 1,5‐ and 2,5‐disubstituted tetrazoles, in various ratios. In this overview, reactions with high or unusual regioselectivities are described, with comments on the possible mechanisms. Microwave‐assisted approaches to the synthesis and functionalization of 5‐substituted tetrazoles are also included.

show abstract

Section: Methods Using Organometallic and Organosilicon Azidesmentioning

confidence: 99%

Synthesis and Functionalization of 5‐Substituted Tetrazoles

2012

View full text Add to dashboard Cite

show abstract

“…Palladium catalyzed the cross-coupling of aryl iodides and alkenyl triflates with dipinacolyldiborane, pinacolborane, and bis(neopentyl glycato)diboron producing aryl-and alkenylpinacolyl boronic esters [156,168,581,584,585] and this type of reaction was used in synthesis of isocomplestatin [244], diazonamide A [221], dityrosine, trityrosine, pulcherosine [222], biphenomycin B [246], spirofungins [228], toward apoptolidin [234] and CB92834 [237]. N,N-Diisopropylaminoboranes can also be used as the boron source [586].…”

Section: Carbon-tin -Silicon -Phosphorous -Arsenic -Antimony -Sementioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…Bis(tributyltin) oxide has also been used as a catalyst in the reaction between nitriles and trimethylsilyl azide to produce tetrazoles 11 and 12 (Scheme 15.7) [15]. Excellent yields of both alkyl and aryl tetrazoles are usually obtained by this method, which avoids the use of hydrazoic acid and also minimizes exposure to toxic tin compounds.…”

Section: Nitriles As Substratesmentioning

confidence: 99%

“…15 N and 13 C NMR spectroscopy are useful tools in the determination of the substitution pattern. The C5 signal in 2-substitued tetrazoles is usually up to 10 ppm deshielded when compared to the 1-substitued tetrazoles.…”

mentioning

confidence: 99%

Five‐Membered Heterocycles with Four Heteroatoms: Tetrazoles

Bhatt

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

Stereoselective synthesis of tetrazole CB92834, a potent retinoid compound

Cited by 20 publications

References 21 publications

Synthesis and Functionalization of 5‐Substituted Tetrazoles

Synthesis and Functionalization of 5‐Substituted Tetrazoles

Transition metals in organic synthesis: Highlights for the year 2005

Five‐Membered Heterocycles with Four Heteroatoms: Tetrazoles

Contact Info

Product

Resources

About