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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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Details

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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