A method for the synthesis of bridged terpenoids

Wiesner, K.; Deljac, A.; Tsai, T. Y. R.; Przybylska, M.

doi:10.1016/s0040-4039(01)97931-6

Cited by 12 publications

(7 citation statements)

References 5 publications

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“…The syntheses of the diketones and the result of this investigation have been reported by Wiesner, Deljac, Tsai & Przybylska (1970).…”

Section: Introductionmentioning

confidence: 89%

The crystal and molecular structure of a tetracyclic diketone, C13O2H16

Przybylska¹

1972

Acta Crystallogr Sect B

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Tetracyclic diketone Cx3OzHx6, m.p. 124°C, was prepared by K. Wiesner, A. Deljac and T.Y.R. Tsai in the process of developing a new stereospecific method for the synthesis of bridged terpenoids. The crystals belong to the space group C2/c with eight molecules in a unit cell of dimensions: a= 16.214 (4), b = 6.194 (4), c = 24" 198 (4) A and fl= 119"06 (3) . The data, consisting of 1563 observed reflexions, were collected with a Picker automatic and a General Electric XRD-5 manual cliffractometer. The structure was solved by the symbolic addition procedure for phase determination for centrosymmetric space groups, and refined by block-diagonal least-squares cycles to a final R value ef 0.042. The molecules are held by the dipole attraction between carbonyl groups.

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“…The syntheses of the diketones and the result of this investigation have been reported by Wiesner, Deljac, Tsai & Przybylska (1970).…”

Section: Introductionmentioning

confidence: 89%

The crystal and molecular structure of a tetracyclic diketone, C13O2H16

Przybylska¹

1972

Acta Crystallogr Sect B

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“…The resulting oil was immediately dissolved in acetone (20 ml) and treated with an excess of Jones' reagent followed by dilution with water and extraction with ether. The ethereal extract was dried, evaporated, and the residue purified by silica gel (35 g, 10% ether-benzene) column chromatography to yield the keto acetate (140) (758 mg, 75%) as a clear oil, homogeneous in t. 1 …”

Section: Preparation Of Keto Acetates (14a and B)mentioning

confidence: 99%

“…A solution of the ketal acetate (1%) (560mg) in 5% methanolic potassium hydroxide (10 ml) was refluxed for 3 h. The solution was cooled, diluted with water, extracted with diethyl ether, dried, and evaporated to furnish the ketal alcohol (16a) (480 mg, 100%) as an oil, homogeneous in t. 1 …”

Section: Preparation Of the Ketal Alcohols (16a And B)mentioning

confidence: 99%

“…The mixture was filtered, diluted with diethyl ether, washed with water, saturated sodium chloride solution, dried, and evaporated to give "natural" tricyclovetivene nor-ketone (29) (77 mg, 99%) as a clear colorless liquid, homogeneous in t. 1 Epimerizafion of "Narural" 29 f o "Nafural" epi-Tricyclove~ivene Nor-ke~one (28) A solution of the "natural" tricyclovetivene nor-ketone (29) (77 mg) in 1% methanolic sodium ethoxide solution (5 ml) was refluxed for 15 h followed by evaporation of the solvent. The residue was diluted with water, extracted with ether, washed with water, saturated sodium chloride solution, dried, and evaporated to give a I : 1 mixture of the epimers (28 and 29).…”

Section: Cleavage O F L O 10 "Na~ural" Tricyclovefiverze Nor-kefone (mentioning

confidence: 99%

“…The ethereal extract was dried and evaporated to yield the "natural" tricyclic alcohol (31) (60 mg, 93%) as an oil, homogeneous in t. 1 By the same method, synthetic nor-ketone (29) (5.2 mg) was converted to the synthetic alcohol (31) (5.6 mg, 100%).…”

Section: Cleavage O F L O 10 "Na~ural" Tricyclovefiverze Nor-kefone (mentioning

confidence: 99%

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A Synthetic Study in the Tricyclovetivene Series

Deljac¹,

Mackay²,

Pan³

et al. 1972

Can. J. Chem.

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Reduction and Related Reactions of α,β‐Unsaturated Carbonyl Compounds with Metals in Liquid Ammonia

Caine

2011

Organic Reactions

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This chapter is concerned with the reduction and related reactions of alpha,beta‐unsaturated ketones by alkali and alkaline earth metals in liquid ammonia. Upon treatment with a metal in liquid ammonia (usually containing an ether co‐solvent) a simple alpha, beta‐unsaturated ketone is converted into the metal enolate corresponding to the saturated ketone. Research during the first half of the 20 th Century revealed that a variety of organic compounds undergo reduction with metals in liquid ammonia but preparative metal‐ammonia reductions of alpha,beta‐unsaturated carbonyl compounds were apparently not described until 1951. In addition to affording a remarkable degree of stereoselectivity, many metal‐ammonia reductions of unsaturated carbonyl systems can be preformed in a variety of functional and protective groupings and the reaction is generally free of the rearrangements sometimes observed when chemical reduction methods are used. The unique features of metal‐ammonia reductions and related reaction have led to their wide application in total synthesis and transformations.

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A method for the synthesis of bridged terpenoids

Cited by 12 publications

References 5 publications

The crystal and molecular structure of a tetracyclic diketone, C13O2H16

The crystal and molecular structure of a tetracyclic diketone, C13O2H16

A Synthetic Study in the Tricyclovetivene Series

Reduction and Related Reactions of α,β‐Unsaturated Carbonyl Compounds with Metals in Liquid Ammonia

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