94344-55-5Relevant academic research and scientific papers
A REARRANGED ABIETANE DITERPENOID FROM THE ROOT OF SALVIA AETHIOPIS
Rodriguez, Benjamin,Fernandez-Gadea, Francisco,Savona, Giuseppe
, p. 1805 - 1806 (1984)
From the root of Salvia aethiopis a new diterpenoid, salvipisone, has been isolated.Its structure, 12-hydroxy-4,5-seco-5,10-friedo-4(18),5(10),6,8,12-abietapentaen-11,14-dione, was established by spectroscopic means and by partial synthesis from aethiopinone.The previously known diterpenoids aethiopinone and royleanone were also found in the same source.Key Word Index -- Salvia aethiopis; Labiatae; diterpenoids; 12-hydroxy-4,5-seco-5,10-friedo-4(18),5(10),6,8,12-abietapentaene-11,14-dione; salvipisone; aethiopinone; royleanone.
Cyclization Reactions of the o-Naphthoquinone Diterpene Aethiopinone. A Revision of the Structure of Prionitin
Cuadrado, Maria J. Sexmero,Torre, Maria C. de la,Lin, Long-Ze,Cordell, Geoffrey A.,Rodriguez, Benjamin,Perales, Aurea
, p. 4722 - 4728 (2007/10/02)
The 4,5-seco-20(10->5)-abeo-abietane derivative aethiopinone (1), a natural o-naphthoquinone isolated from some Salvia species, was subjected to a series of acid-catalyzed reactions which yielded phenalene derivatives (2, 6, 9, and 11) and other cyclization products (3 and 10).The 11-nor derivative 3 is formed by an intramolecular cycloaddition reaction, and a mechanistic pathway for the formation of the phenalene derivatives 6 and 11 is also proposed.These transformations of aethiopinone (1) allowed the partial syntheses of the naturally occuring diterpenes salvipisone (8), salvi lenone (9), and the racemic form of prionitin (11), a rearranged abietane diterpeniod previously isolated from the root of Salvia prionitis, to which structure 12 had been attributed only on the basis of NMR spectroscopic studies.In the light of the results reported herein, including an X-ray analysis of compound 11, the structure 12 assigned to prionitin must be changed to 11.
