35986-56-2

Upstream product

• 22037-28-1 3-bromofurane 
• 130530-09-5 (1S*,3'S*,6R*)-methyl-6-formyl-2,6-dimethylcyclohex-2-ene-1-spiro-2'-oxirane-3'-carboxylate 
• 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 
• 130530-12-0 (1S*,3R*,3aS*,7aS*)-3-acetoxy-1,7a-epoxy-3a,7-dimethyl-1,3,3a,4,5,7a-hexahydro-2H-inden-2-one 
• 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 
• 130530-29-9 (1S*,3R*,3aS,7aS*)-β-1,7a-epoxy-3-hydroxy-3a,7-dimethyl-1,3a,4,5-hexahydro-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 

Relevant academic research and scientific papers

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).