Enolate alkylation of bicyclo(2.2.2)oct-5-en-2-one and radical cyclisation - a potential approach for the construction of tricyclic carbocycles

Rajamannar, T.; Balasubramanian, K. K.

doi:10.1016/s0040-4039(00)82193-0

Cited by 23 publications

(14 citation statements)

References 5 publications

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“…[15] Having secured the 1-bromo-2-(bromomethyl)cyclohex-1-ene (14), it was coupled with the bicyclic ring system 5 to obtain 15 in 70 % yield (Scheme 3). The next step, a five-membered ring annulation was carried out by using the metal/halogen exchange methodology.…”

Section: Resultsmentioning

confidence: 99%

Utilization of the Versatility of Sulfur in C–C Bond Formation and Cleavage: Synthesis of ABC Taxoid Skeletons

Sonawane¹,

Kalkote²,

Sudrik³

et al. 2007

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

Utilization of the Versatility of Sulfur in C–C Bond Formation and Cleavage: Synthesis of ABC Taxoid Skeletons

Sonawane¹,

Kalkote²,

Sudrik³

et al. 2007

Eur J Org Chem

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“…ICN Silica gel (particle size 0.032-0.063 mm) was used for flash column chromatography. Analytical chiral HPLC was performed on a Chiralcel OD-H column (250 mm x 4.6 mm, 5 μm particle size, 0.8 mL/min flow rate) obtained from Daicel Chemical Industries, Ltd. 1 (2-Bromocyclohex-1-enyl)methanol (9). [1,2] The allylic alcohol was synthesized according to a similar procedure.…”

Section: Methodsmentioning

confidence: 99%

“…Analytical chiral HPLC was performed on a Chiralcel OD-H column (250 mm x 4.6 mm, 5 μm particle size, 0.8 mL/min flow rate) obtained from Daicel Chemical Industries, Ltd. 1 (2-Bromocyclohex-1-enyl)methanol (9). [1,2] The allylic alcohol was synthesized according to a similar procedure. [3] To a solution of DMF (7.4 mL, 95.0 mmol, 3.0 equiv) in CHCl 3 (25 mL) was added PBr 3 (8.1 mL, 86.0 mmol, 2.7 equiv) dropwise at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The filtrate was concentrated and the crude product was used in the next step without further purification. R f = 0.80 (4:1 hexanes/EtOAc); 1 The crude product was dissolved in Et 2 O (60 mL) and the solution was cooled to 0 °C. DIBAL (5.7 mL, 32.0 mmol, 1.0 equiv) was added slowly, and the mixture was stirred at 25°C…”

Section: Supplementary Materials (Esi) For Organic and Biomolecular Chemmentioning

confidence: 99%

“…The filtrate was concentrated, and the residue was purified by flash chromatography (8:1 hexanes/EtOAc) to give 22 as a colorless oil (46 mg, 94% yield). R f = 0.28 (7:1 hexanes/EtOAc); 1 55 (m, 12H) The compound was recrystallized from ethyl acetate/heptane to provide crystals suitable for x-ray analysis.…”

Section: S14mentioning

confidence: 99%

See 2 more Smart Citations

Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis

Baumgartner

Liu

et al. 2010

Org. Biomol. Chem.

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Radical Cyclization Reactions

et al. 1996

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Radical cyclization reactions are among the most powerful and versatile methods for the construction of mono‐ and polycyclic systems. The advantages these reactions offer to the synthetic organic chemist include high functional group tolerance and mild reaction conditions combined with high levels of regio‐ and stereochemistry. Furthermore, the recent progress in radical chemistry has led to the development of a broad range of very useful practical methods to conduct radical cyclization reactions. In general, radical cyclization reactions comprise three basic steps: selective radical generation, radical cyclization, and conversion of the cyclized radical to the product. For the generation of the initial radical a broad variety of suitable precursors can be employed, such as halides, thio‐ and selenoethers, alcohols, aldehydes and hydrocarbons. The cyclization step usually involves the intramolecular addition of a radical to a multiple bond. Most often carbon–carbon multiple bonds are employed; however, there are also examples known for the addition to carbon–oxygen and carbon–nitrogen bonds. Depending on the method employed, the cyclized radical is converted to the desired product by trapping with a radical scavenger, by a fragmentation reaction, or by an electron transfer reaction. The section Mechanism, Regio‐ and Stereochemistry provides an introduction to the key features of radical cyclization with a special emphasis on the factors controlling the regio‐ and stereochemistry. The section Scope and Limitations covers the different methods used to conduct radical cyclization. The basic principles of radical chemistry and general practical considerations when conducting radical cyclizations are not discussed in detail. Several excellent review articles and books dealing with these topics are available.

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Enolate alkylation of bicyclo(2.2.2)oct-5-en-2-one and radical cyclisation - a potential approach for the construction of tricyclic carbocycles

Cited by 23 publications

References 5 publications

Utilization of the Versatility of Sulfur in C–C Bond Formation and Cleavage: Synthesis of ABC Taxoid Skeletons

Utilization of the Versatility of Sulfur in C–C Bond Formation and Cleavage: Synthesis of ABC Taxoid Skeletons

Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis

Radical Cyclization Reactions

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