5956-05-8

Upstream product

• 917-54-4 methyllithium 
• 78-94-4 methyl vinyl ketone 
• 66289-26-7 α-1-Methyl-2-formyl-3-isopropylcyclopentan 
• 74654-57-2 (1R,5S)-1-Isopropyl-8-methyl-4-methylene-spiro[4.5]dec-8-en-7-one 
• 74654-57-2 (1S,5S)-1-Isopropyl-8-methyl-4-methylene-spiro[4.5]dec-8-en-7-one 
• 87017-52-5 6-methylbicyclo<3.3.0>oct-1(5)-en-2-one 
• 28296-85-7 (+/-)-β-acorenol 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 66245-17-8 (1S,4S,5S)-1-Isopropyl-7-methoxy-4,8-dimethyl-spiro[4.5]dec-6-en-8-ol 
• 58649-46-0 (1R,4S,5S)-1-Isopropyl-4,10,10-trimethyl-8,12-dioxa-dispiro[4.1.5.3]pentadecane 
• 56326-39-7 Spiro-<4,5>-decanon (trans) 
• 6784-16-3 5-methyl-2-isopropylidenecyclopentanone 
• 58649-47-1 2-Isopropyl-5-methyl-1-(3-methyl-pent-4-enyl)-cyclopentanol 
• 6784-18-5 2-isopropyl-5-methylcyclopentanone 

Downstream Products

• 5956-05-8 4-epi-acorenone 

Relevant academic research and scientific papers

Studies on metabolites of mycoparasitic fungi. III. New sesquiterpene alcohol from Trichoderma koningii

A new sesquiterpene alcohol, named tricho-acorenol (1), was isolated from the culture broth of Trichoderma koningii OUDEMANS along with methyl benzoate (2), cyclonerodiol (3), cyclo-(L-Pro-L-Leu) (4), 4-hydroxyphenethyl alcohol (5), uracil (7), and a ceramide (6). The ceramide (6) was identified as (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octadecanetriol by the use of ion-spray ionization MS (ISI-MS) and comparison of the optical rotation and the 1H-NMR data with those of (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol. The structure of tricho-acorenol was elucidated to be (1S,4S,5S,7R)-1-isopropyl-4,8-dimethyl-spiro-[4.5]dec-8-en-7-ol on the basis of chemical and spectroscopic evidence.

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).

SPIRODECANES BY PHOTOANNELATION. TOTAL SYNTHESIS OF (-)-ACORENONE

An efficient synthesis of the optically active spirodecane sesquiterpene acorenone is described.The key carbon-carbon bonds are formed by a (2+2) photochemical cycloaddition between 2,2-dimethyl-3(2H)-furanone and an alkene derived from limonene.