81369-46-2

Basic information

• Product Name: (+)-valdiviolide
• CAS NO: 81369-46-2
• Molecular Weight: 250.338
• Mol File: 81369-46-2.mol

Chemical Properties

• CAS DataBase Reference: (+)-valdiviolide(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-valdiviolide(81369-46-2)
• EPA Substance Registry System: (+)-valdiviolide(81369-46-2)

Safety Data

• Hazardous Substances Data: 81369-46-2(Hazardous Substances Data)

Upstream product

• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 89708-57-6 (4aS,8aS)-2-[1-Butylsulfanyl-meth-(E)-ylidene]-5,5,8a-trimethyl-octahydro-naphthalen-1-one 
• 77630-13-8 (4aS,8aS)-5,5,8a-Trimethyl-1-oxo-decahydro-naphthalene-2-carbaldehyde 
• 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 
• 16776-05-9 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one 
• 50490-43-2 (+/-)-euryfuran 

Downstream Products

• 4795-87-3 (+)-winterin 

Relevant articles and documents

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