1684-54-4Relevant academic research and scientific papers
The structure of laricinolic acid and its biomimetic transformation into officinalic acid
Erb, Bernhard,Borschberg, Hans-Juerg,Arigoni, Duilio
, p. 2307 - 2309 (2007/10/03)
Laricinolic acid (8), a new sesquiterpene of the drimane type, has been isolated from the wood-rotting fungus Laricifomes officinalis. Its structure was elucidated by spectroscopic means and confirmed via a correlation with the known drimenine derivative 13. Oxidation of 8 to 1, followed by a mild thermal treatment, furnished (-)-officinalic acid (4) in 65% yield. This transformation establishes the hitherto unknown absolute configuration of the latter. An independent correlation was achieved by pyrolysis of 4 which furnished (-)-dihydrooxoisodrimenine (14) of known absolute configuration.
A NEW AND EFFICIENT ROUTE TO OPTICALLY ACTIVE DRIMANES. SYNTHESIS OF (+)-WINTERIN, (+)-CONFERTIFOLIN, (+)-ISODRIMENIN, AND (+)-BICYCLOFARNESOL
Hueso-Rodriguez, Juan A.,Rodriguez, Benjamin
, p. 1567 - 1576 (2007/10/02)
The drimane sesquiterpenes (+)-winterin, (+)-confertifolin, (+)-isodrimenin, and (+)-bicyclofarnesol were synthesised starting from royleanone, an abietane diterpenoid easily available as a main constituent of the root of some Salvia species.
A new approach to annelated butenolides. The total synthesis of (+/-)-isodrimenin
Jansen, B. J. M.,Peperzak, R. M.,Groot, Ae. de
, p. 505 - 508 (2007/10/02)
A new approach to annelated butenolides has been developed starting from trans-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-naphthalenone (3) and cyclohexanones.A reaction sequence consisting of formylation of the enolates of these ketones, protection of the formyl group as its dioxolane and addition of methoxy(phenylthio)methyllithium has been used to introduce the necessary functionalized carbon atoms.Rearrangement of the adduct to α-(phenylthio)aldehydes, followed by hydrolysis of the dioxolane, resulted in the formation of butenolides.The method has been demonstrated in the total synthesis of (+/-)-isodrimenin.Direct hydrolysis of the adducts, obtained after addition of methoxy(phenylthio)methyllithium, followed by treatment with acid, also gave butenolides.
Synthesis of the Drimane-related Sesquiterpenes Euryfuran, Confertifolin, and Valdiviolide
Ley, Steven V.,Mahon, Michael
, p. 1379 - 1381 (2007/10/02)
trans-3,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethylnaphthalene-1-(2H)-one (1) was converted into the drimane sesquiterpene euryfuran (5) in 59percent yield.Euryfuran was then used as a starting material for the synthesis two other drimane natural products, confertifolin and valdiviolide.The preparation of valdiviolide constitutes the first total synthesis of this molecule.
SYNTHESIS OF EURYFURAN, VALDIVIOLIDE, AND CONFERTIFOLIN
Ley, Steven V.,Mahon, Michael
, p. 4747 - 4750 (2007/10/02)
Starting from 5,5,9-trimethyl-trans-1-decalone (4), short and highly efficient synthesis of three drimane natural products, euryfuran (1), valdiviolide (2), and confertifolin (3) have been developed.
