4795-87-3Relevant articles and documents
Synthesis of Drimanic Sesquiterpenes, (+)-Valdiviolide, (+)-12α-Hydroxyisodrimenin and (+)-Winterin
Nakano, Tatsuhiko,Villamizar, Jose,Maillo, Maria Aracelis
, p. 560 - 561 (2007/10/03)
The synthesis of (+)-valdiviolide 6a, (+)-12α-hydroxyisodrimenin 7 and (+)-winterin 8, from manool 1 is described.
Influence of Electron Donating Aromatic Substituents on the Ruthenium Tetroxide-Catalysed Oxidation of (+/-)-Podocarpa-8,11,13-trienes
Ghosh, Sukumar,Ghatak, Usha Ranjan
, p. 7289 - 7296 (2007/10/02)
Whereas the (+/-)-podocarpa-8,11,13-trienes 3b-e, incorporating a phenolic hydroxyl or methyl ether functionality at C-11 and C-14, and C-14 respectively, on oxidation with sodium metaperiodate - catalyzed by ruthenium tetroxide give (+/-)-winterin, through chemoselective degradation of the aromatic ring, the unsubstituted 3a, isomeric methyl ethers 3f-i, and cis-podocarpa-8,11,13-triene undergo only benzylic oxidation resulting in the respective ketones 8d, 8a-c, 8e and the diketone 9.Similar oxidation reaction of the hexahydrophenanthrene 7a led to the α,β-unsaturated tricyclic ketone 11a and the tetrahydronaphthalene dicarboxylic anhydride 12.In contrast, 7b produced the diketone 10b and the α,β-unsaturated ketone 11b as the sole isolated products.
Synthesis of Winterin from Podocarpic Acid
Bendall, Justin G.,Cambie, Richard C.,Grimsdale, Andrew C.,Rutledge, Peter S.,Woodgate, Peul D.
, p. 1063 - 1067 (2007/10/02)
Ozonolysis of a hydroquinone derived from podocarpic acid (1) gave the biologically active natural product winterin (11).Treatment of the quinone (12) with ozone bave a ring-contracted spiro furanone, the mechanism of formation of which is proposed.
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.
OZONOLYSIS OF PHENOLIC DEHYDROABIETANE DERIVATIVES. - SYNTHESES OF OPTICALLY ACTIVE (+)-CONFERTIFOLIN, (+)-VALDIVIOLIDE, (+)-WINTERIN, (+)-ISODRIMERIN, AND (+)-PALLESCENSIN A-
Akita, Hiroyuki,Oishi, Takeshi
, p. 1580 - 1587 (2007/10/02)
Ozonolysis of phenolic dehydroabietane derivatives was investigated and the products obtained by cleavage of the aromatic ring were found to be determined by the hydroxyl substitution pattern of the aromatic C-ring.Ozonolysis of the 12-hydroxy compound (ferruginol (12) gave pentanorlabdane-type compounds (14, 15, and 16).Ozonolysis of the 11-hydroxy derivative (18) and/or the 14-hydroxy derivatives (19 and 20 afforded optically active drimanic sesquiterpenes ((+)-isodrimenin (8), (+)-confertifolin (7), (+)-valdiviolide (9), and (+)-winterin (10) in one step.In this case, the mode of cleavage was different from that of 12.On the other hand, ozonolysis of the 13-hydroxy compound (3) caused cleavage in yet another manner to give the butenolide (23), which was easily converted into optically active pallescensin A (11).The mechanisms of the cleavage reactions are discussed.Keywords: - aromatic ring cleavage; ozonolysis; drimanic sesquiterpenes; phenolic diterpenes; catechol