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Digitale Medien

A McMurry Route to the Dienediyne Portion of Models of the Neocarzinostatin Chromophore (1998)

Rank, Elisabeth ; Brückner, Reinhard

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1045-1053

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Details

ISSN: 1434-193X

Schlagwort(e): C, C couplings ; Cycloaromatization ; Dienediynes ; McMurry reaction ; Neocarzinostatin ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The 6-ring/10-ring dienediyne model 11 of the antitumor agent neocarzinostatin chromophore 1 and its 6-ring/11-ring homolog 12 have been obtained in 41 and 18% yields, respectively, by McMurry cyclizations of ketoaldehydes 8 and 9 using TiCl3·2DME and Zn/Cu couple. Compounds 8 and 9 were obtained by multistep syntheses starting from the readily available acetylenic aldehydes HC≡CC(CH3)2-(CH2)nCH=O (18, n = 1; 21, n = 2). Dienediyne 11 was converted into the dienediyne ketone 33 which cycloaromatized at room temperature giving the octahydrophenanthrone 35 in 16% yield.

Materialart: Digitale Medien

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