6754-56-9

Upstream product

• 5750-64-1 trans-1,2,3,4,9,10,11,12-Octahydro-8-hydroxy-1,1,12-trimethyl-phenanthren 
• 62691-12-7 12-methoxy-8,12-abietadiene-11,14-dione 
• 16826-80-5 12-methoxypodocarpa-8,12-diene-11,14-dione 
• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 218780-16-6 (+)-12α-hydroxyisodrimenin 
• 24173-70-4 (+)-valdiviolide 
• 142791-55-7 12-methoxypodocarpa-8,11,13-triene-11,14-diol 
• 37866-99-2 royleanone 
• 64597-80-4 (+/-)-11,14-Dihydroxypodocarpatriene 
• 106623-26-1 (4aR,10aR)-5,8-Dimethoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene 
• 5720-79-6 (+/-)-14-methoxypodocarpa-8,11,13-triene 

Downstream Products

• 1684-54-4 (+)-isodrimenin 
• 1811-23-0 (+)-confertifoline 

Relevant academic research and scientific papers

Synthesis of Drimanic Sesquiterpenes, (+)-Valdiviolide, (+)-12α-Hydroxyisodrimenin and (+)-Winterin

The synthesis of (+)-valdiviolide 6a, (+)-12α-hydroxyisodrimenin 7 and (+)-winterin 8, from manool 1 is described.

Synthesis of Winterin from Podocarpic Acid

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.

Influence of Electron Donating Aromatic Substituents on the Ruthenium Tetroxide-Catalysed Oxidation of (+/-)-Podocarpa-8,11,13-trienes

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.

A NEW AND EFFICIENT ROUTE TO OPTICALLY ACTIVE DRIMANES. SYNTHESIS OF (+)-WINTERIN, (+)-CONFERTIFOLIN, (+)-ISODRIMENIN, AND (+)-BICYCLOFARNESOL

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-

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