28296-85-7

Upstream product

• 74320-28-8 (1R^*,3aR^*,5aR^*,9aR^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 917-64-6 methyl magnesium iodide 
• 4709-59-5 ethyl 2-(1-cyclohexenyl)acetate 
• 917-54-4 methyllithium 
• 132557-04-1 (1R,4S,5S)-4,8-Dimethyl-spiro[4.5]dec-7-ene-1-carboxylic acid 2-hydroxy-ethyl ester 
• 74320-29-9 rac-(1R,3aS,5aS,9aR)2,3,3a,4,6,9-hexahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 43219-77-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4-methyl-8-methylenespiro<4.5>dec-6-ene 
• 65408-94-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>deca-6,8-diene 
• 955007-45-1 C₁₃H₁₈O₃ 
• 955007-44-0 C₁₅H₂₂O₃ 
• 43219-78-9 2-Cyclohex-1-enyl-hex-5-enoic acid ethyl ester 
• 132557-02-9 (3aR,4R,6aS)-3a-But-3-enyl-4-methyl-hexahydro-pentalen-1-one 

Downstream Products

• 28400-12-6 β-alaskene 
• 24048-44-0 (+/-)-β-acoradiene 
• 24048-44-0 α-alaskene 
• 5956-05-8 (+/-)-acorenone 
• 24048-44-0 (+/-)-4-epi-β-acoradiene 
• 5956-05-8 (+/-)-acorenone B 
• 5956-05-8 4-epi-acorenone 

Relevant academic research and scientific papers

Total syntheses of (±)-α-acorenol, β-acorenol, α-epi-acorenol and β-epi-acorenol via an Ireland ester Claisen rearrangement and RCM reaction sequence

Total syntheses of (±)-α- and β-acorenols and (±)-α- and β-epi-acorenols, spiro[4.5]decane sesquiterpenes, isolated from the western Australian sandalwood oil, have been accomplished employing a combination of Ireland ester Claisen rearrangement and RCM r

Stereocontrolled Synthesis of (+/-)-Acorenone B Based on New Ring Conversion

On the basis of a new ring conversion reaction from the bicyclooctane ring to the spirodecane ring, (+/-)-acorenone B was synthesized in a stereocontrolled fashion.

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. Total Synthesis of (+/-)-Acorenone

The metal-ammonia reduction of the cyclopentabenzofuran derivative (2b) afforded a mixture of 4-epi-β-acorenol (5), a disubstituted olefin (8) as the main product, and a perhydro compound (9).Compound 8 was converted to 5 via the exo-diene (15).Dehydration of 5 afforded the 4-epi-β-acoradiene (6), selective reduction of which gave the monoolefin (7), and then the allylic oxidation of 7 gave (+/-)-acorenone (3) in good yield.Keywords - acorane-alaskane sesquiterpene; acorenone; cyclopentabenzofuran; total synthesis; 4-epi-β-acorenol; 4-epi-α-acorenol; 4-epi-β-acoradiene; metal-ammonia reduction; conjugate reduction; terminal olefin reduction.

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. I. Total Synthesis of (+/-)-β-Acorenol

(+/-)-β-Acorenol (2) was synthesized by the methal-ammonia reduction of (1R*,3aR*,5aR*,9aR*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran (11a), which was prepared from the spirodienone

Novel Cyclopentabenzofuran Intermediates for the Synthesis of Acorane-Alaskane Sesquiterpenes: Total Synthesis of (+/-)-β-Acorenol and (+/-)-Acorenone

Cyclopentabenzofuran derivatives (5a) and (5b) were synthesized from spirodienone esters (6a) and (6b), respectively, and the utility of these intermediates in acorane-alaskane sesquiterpene synthesis is illustrated by their conversion into (+/-)-β-acorenol (4a) and (+/-)-acorenone (1).