130530-19-7

Basic information

• Product Name: (1R*,3S*,3aS*,4R*,5R*,7aS*)-1-acetoxy-5-bromo-3,3a-epoxy-4-hydroxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one
• CAS NO: 130530-19-7
• Molecular Weight: 333.179
• Mol File: 130530-19-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R*,3S*,3aS*,4R*,5R*,7aS*)-1-acetoxy-5-bromo-3,3a-epoxy-4-hydroxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R*,3S*,3aS*,4R*,5R*,7aS*)-1-acetoxy-5-bromo-3,3a-epoxy-4-hydroxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one(130530-19-7)
• EPA Substance Registry System: (1R*,3S*,3aS*,4R*,5R*,7aS*)-1-acetoxy-5-bromo-3,3a-epoxy-4-hydroxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one(130530-19-7)

Safety Data

• Hazardous Substances Data: 130530-19-7(Hazardous Substances Data)

Upstream product

• 52527-81-8 (1R*,4S*,7aR*)-1-acetoxy-4,7a-dimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one 
• 52527-81-8 Acetic acid (4R,7aS)-4,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-1-yl ester 
• 130530-14-2 (1R*,4R*,5S*,7aR*)-1-acetoxy-4,5-epoxy-4,7a-dimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one 
• 130530-16-4 (1R*,2R*,3R*,3aS*,4S*,5S*,7aS*)-1-acetoxy-3,3a;4,5-diepoxy-4,7a-dimethyl-2,3,3a,4,5,6,7,7a-octahydro-1H-indene 
• 130530-15-3 (1R*,2S*,4R*,5S*,7aR*)-1-acetoxy-4,5-epoxy-4,7a-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-2-ol 
• 118198-52-0 (1R*,4R*,7aR*)-1-acetoxy-4-bromo-4,7a-dimethyl-1,4,5,7,7a-hexahydro-2H-inden-2-one 
• 130530-11-9 (1R*,2S*,7aR*)-1-acetoxy-4,7a-dimethyl-2,6,7,7a-tetrahydro-1H-inden-2-ol 
• 118198-54-2 (1R*,7aR*)-1-acetoxy-4,7a-dimethyl-1,6,7,7a-tetrahydro-2H-inden-2-one 
• 52527-82-9 (1R*,4S*,7aR*)-1-hydroxy-4,7a-dimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one 
• 130530-10-8 (1R*,3S*,3aS*,4S*,7aS*)-1-acetoxy-3,3a;4,5-diepoxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one 

Downstream Products

• 130530-21-1 Acetic acid (1aS,3R,3aS,6R,7R,7aS)-6-bromo-3-hydroxy-3a,7-dimethyl-2-oxo-octahydro-1-oxa-cyclopropa[c]inden-7-yl ester 
• 130530-20-0 (1R*,3R*,3aS*,4R*,5R*,7aS*)-1,4-diacetoxy-5-bromo-3,3a-epoxy-4,7a-dimethyl-1,3,3a,4,5,6,7,7a-octahydro-2H-inden-2-one 

Relevant articles and documents

Synthetic Studies on Terpenoid Compounds. Part 27. Total Synthesis of Calodendrolide

A synthesis of calodendrolide (1) was explored starting from 4,7a-dimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one (4).The synthesis of key aldehyde ester (5) by a route involving derivation of α,β;γ,δ-diepoxy compound (8) and selective removal of the γ,δ-epoxy group failed.The second approach was based on the regio- and stereo-selective epoxidation of derived dienol (9), making use of the orientation effect of the hydroxy group, which successfully gave α,β-epoxidised derivative (10) with correct stereochemistry.Treatment of the key intermediate (5), obtained from compound (10), with 3-lithiofuran afforded (+/-)-calodendrolide (1) together with its epimer (6).