20489-24-1

Basic information

• Product Name: (4aR)-3,4aβ,5β-Trimethyl-4a,5,6,7-tetrahydronaphtho[2,3-b]furan-2(4H)-one
• Synonyms: (4aR)-3,4aβ,5β-Trimethyl-4a,5,6,7-tetrahydronaphtho[2,3-b]furan-2(4H)-one;(4aR)-4a,5,6,7-Tetrahydro-3,4a,5β-trimethylnaphtho[2,3-b]furan-2(4H)-one;(R)-Ligularenolide;Ligularenolide
• CAS NO: 20489-24-1
• Molecular Formula: C15H18O2
• Molecular Weight: 230.30222
• Mol File: 20489-24-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4aR)-3,4aβ,5β-Trimethyl-4a,5,6,7-tetrahydronaphtho[2,3-b]furan-2(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aR)-3,4aβ,5β-Trimethyl-4a,5,6,7-tetrahydronaphtho[2,3-b]furan-2(4H)-one(20489-24-1)
• EPA Substance Registry System: (4aR)-3,4aβ,5β-Trimethyl-4a,5,6,7-tetrahydronaphtho[2,3-b]furan-2(4H)-one(20489-24-1)

Safety Data

• Hazardous Substances Data: 20489-24-1(Hazardous Substances Data)

Upstream product

• 130395-64-1 10β-hydroxy-8β-methoxyeremophilenolide 
• 105088-15-1 (4aR,5S)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone 
• 197709-21-0 (4aR,5S)-4a,5-Dimethyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one 
• 160837-37-6 (4aR,5S,7S)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-7-isopropenyl-naphthalene-2(3H)-one 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 92574-17-9 8β-hydroxy-eremophil-7(11),9(10)-dien-12,8-olide 
• 55050-23-2 3,3-ethylenedioxy-4β,5β-dimethyloctalin-9-en-8-one 
• 77311-88-7 3,3-ethylenedithio-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 77311-80-9 3,3-ethylenedioxy-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 77311-86-5 4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-3,8-dione 
• 55050-26-5 5β,6β-dimethyl-2,7-dioxo-Δ^(1(10))-octalin 
• 77311-89-8 3,3-ethylenedithioligularenolide 

Downstream Products

• 4871-90-3 (+/-)-Tetrahydroligularenolid 
• 29395-64-0 (-)tetrahydroligularenolide 

Relevant articles and documents

ABSOLUTE CONFIGURATION OF EREMOPHILENOLIDES FROM HERTIA CHEIRIFOLIA

The absolute configurations of 8α-methoxy-10β-hydroxyeremophilenolide and 8β,10β-dihydroeremophilenolide from Hertia cheirifolia were determined by transformation into (-)tetrahydroligularenolide.

Enantioselective synthesis of R-(-)-ligularenolide starting from S-(+)-carvone

The first enantioselective synthesis of R-(-)-ligularenolide 1 starting from S-(+)-carvone 2 is described.

Enantioselective synthesis of R-(-)-ligularenolide and the progesterone receptor ligand R-(-)-PF1092C starting from S-(+)-carvone

A new enantioselective synthesis of cremophilane sesquiterpenes was developed starting from S-(+)-carvone 3, using a conjugate addition- annelation sequence. The synthesis of R-(-)-ligularenolide 1 was accomplished in a staightforward manner with the annelation of the lactone as the last step. For the synthesis of the progesterone receptor ligand R-(-)-PF1092C 2 a different strategy was followed in which first the lactone was annelated. The concomitant isomerization of the double bond of the isopropenyl group into the conjugate position then offered an alternative way to remove the side chain and simultaneously provide for an ideal functionally for the introduction of the cis β-diol function at the C2,C3 position.