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Digitale Medien

Chirale Phthalid-Aromastoffe: (3a–7a)-cis-3-Butylhexahydrophthalid-Stereoisomere in Knollensellerie (Apium graveolens L var.rapaceum) (1996)

Manzardo, Giuseppe G. G. ; Kürsteiner-Laube, Sandra ; Perrin, Daniel

Springer

European food research and technology 203 (1996), S. 501-506

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ISSN: 1438-2385

Schlagwort(e): Celeriac ; (3a–7a)-cis-3-Butylhexahydrophthalides ; Relative configuration ; NOE difference spectroscopy ; Enantioselective GC

Quelle: Springer Online Journal Archives 1860-2000

Thema: Werkstoffwissenschaften, Fertigungsverfahren, Fertigung

Notizen: Abstract In diethyl ether extracts from celeriac (Apium graveolens L. var.rapaceum) all four stereoisomers of (3a–7a)-cis-3-butylhexahydrophthalide were found to be present. The analyses were carried out by means of GC, enantioselective GC and GC-MS. The assignment of the relative configuration of the diastereomers3 and4 was accomplished by NOE difference spectroscopy.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1007/BF01193153

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Digitale Medien

Formale Totalsynthese von (±)-Isocomen durch Anwendung der α-Alkinon-Cyclisierung (1986)

Manzardo, Giuseppe G. G. ; Karpf, Martin ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 69 (1986), S. 659-669

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Formal Total Synthesis of (±)-Isocomen by Application of the α-Alkinon CyclizationA total synthesis of the racemic form of the sesquiterpene isocomene (A) was accomplished by application of the cyclopentenone anellation B→D (Scheme 1) which includes the α-alkynone cyclization C→D, a gas-phase flow thermolytic process. Starting with the known product 2 (Scheme 3) of the anellation B→D, the elaboration of ring C of A proceeded in 9 steps to the α-alkynone 16 (Scheme 5) which was cyclized at 540° selectively to give the angularly fused triquinane 4 (77%). A two-step procedure then led to 5 (Scheme 6), a last but one intermediate in a known total synthesis of (±)-A. The conversion of 16 to 4 also demonstrated the compatibility of an acetoxy function with the anellation sequence B→D.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19860690316

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Digitale Medien

Anwendung der α-Alkinon-Cyclisierung: Totalsynthese von (±)-Alben (1983)

Manzardo, Giuseppe G. G. ; Karpf, Martin ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 66 (1983), S. 627-632

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Application of the α-Alkynone Cyclization: Total Synthesis of (±)-AlbeneA synthesis of the racemic form of the natural tricyclic hydrocarbon albene (1) from the Diels-Alder adduct 2 of tiglyl chloride and cyclopentadiene is described (24% yield). The key step 5→6 involves a thermal α-alkynone cyclization (Scheme 3), which is able to establish a new quarternary C-atom at an unactivated position with a high degree of regiospecificity.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19830660224

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