24173-70-4

Upstream product

• 50490-43-2 (+/-)-euryfuran 
• 16776-05-9 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one 
• 81306-30-1 (5aR,9aR)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 77630-13-8 (4aS,8aS)-5,5,8a-Trimethyl-1-oxo-decahydro-naphthalene-2-carbaldehyde 
• 89708-57-6 (4aS,8aS)-2-[1-Butylsulfanyl-meth-(E)-ylidene]-5,5,8a-trimethyl-octahydro-naphthalen-1-one 
• 67919-45-3 (+)-euryfuran 
• 16776-06-0 2-Hydroxymethylen-5,5,9-trimethyl-trans-decalon 
• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 81306-30-1 (5aS,9aS)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 81306-29-8 2-(butylthiomethylene)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 

Downstream Products

• 4795-87-3 (+)-winterin 

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 the Drimane-related Sesquiterpenes Euryfuran, Confertifolin, and Valdiviolide

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

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.

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