Etude de la préparation de systèmes décaliniques fonctionnalisés par réaction d'électrocyclisation

Leclaire, M.; Jean, P.; Lopez, Roman; Ricard, Louis; Plessix, H.; Lallemand, Jean‐Yves

doi:10.1016/0040-4020(95)00357-e

Cited by 7 publications

(2 citation statements)

References 15 publications

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“…Ester 7a failed to react with the NCS-thiophenol reagent combination 21 but a smooth reaction occurred with freshlyprepared phenylsulfenyl chloride, 22 and crystalline lactone 9a could be isolated in excellent (89%) yield on a 20 g scale. Slightly lower yields of lactone could be obtained using the more convenient in situ method of Suzuki et al (PhSSPh, SO 2 Cl 2 , DCM).…”

Section: Resultsmentioning

confidence: 99%

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

et al. 2005

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A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts which could be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1(C)B or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

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Section: Resultsmentioning

confidence: 99%

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

et al. 2005

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“…Treatment of the acetate 11 with Pd(PPh 3 ) 4 and SmI 2 led to cyclopropane ring opening and concomitant elimination of the acetate . Other methods of transforming propargylic acetates to allenes were tried with little or no success . We were gratified to find that Strykers' reagent [(PPh 3 )CuH] 6 delivers a hydride to afford the desired allene 12 without serious complications .…”

Section: Resultsmentioning

confidence: 99%

A Rapid Synthesis of Hydroxymethylacylfulvene (HMAF) Using the Allenic Pauson−Khand Reaction. A Synthetic Approach to Either Enantiomer of This Illudane Structure

Brummond

Petersen

2000

J. Am. Chem. Soc.

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An allenic Pauson−Khand reaction has been employed in the preparation of (±)-hydroxymethylacylfulvene (HMAF), an anticancer agent that is currently in Phase II clinical trials for a variety of solid tumor types. The synthesis is effected in 11 steps from commercially available starting materials. In addition, an asymmetric route to the title compound has been established by intersecting the racemic synthesis with an enantiomerically pure intermediate. The preparation of the enantiomerically pure intermediate involved the Sharpless asymmetric dihydroxylation (AD) of a trisubstituted olefin of an enyne system. This approach provides access to both enantiomers of HMAF simply by changing the ligands in the Sharpless AD reaction. Optimized conditions for the stereospecific synthesis of E or Z trisubstituted enynes from an aliphatic ketone using either Peterson olefination or Horner−Wadsworth−Emmons protocols are reported. Finally, a better understanding of the stereoelectronic requirements of the allenic P−K reaction is recognized.

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ChemInform Abstract: Study on the Preparation of Functionalized Decalinic Systems by Electrocyclization Reaction.

et al. 1995

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Etude de la préparation de systèmes décaliniques fonctionnalisés par réaction d'électrocyclisation

Cited by 7 publications

References 15 publications

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

A Rapid Synthesis of Hydroxymethylacylfulvene (HMAF) Using the Allenic Pauson−Khand Reaction. A Synthetic Approach to Either Enantiomer of This Illudane Structure

ChemInform Abstract: Study on the Preparation of Functionalized Decalinic Systems by Electrocyclization Reaction.

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