21653-33-8

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Acorenone B is used as a bioactive molecule for its potential roles in treating neurological disorders and promoting gastrointestinal health due to its pharmacological properties.
Used in Agricultural Industry:
(+)-Acorenone B is used as an antifungal, antimicrobial, and insecticidal agent to protect crops and maintain their health, contributing to sustainable agriculture practices.
Research on (+)-Acorenone B continues to explore its potential applications in both the pharmaceutical and agricultural industries, highlighting its multifaceted utility.

InChI:InChI=1/C15H24O/c1-10(2)13-6-5-12(4)15(13)8-7-11(3)14(16)9-15/h7,10,12-13H,5-6,8-9H2,1-4H3/t12-,13-,15?/m0/s1

Upstream product

• 917-54-4 methyllithium 
• 78-94-4 methyl vinyl ketone 
• 66289-26-7 α-1-Methyl-2-formyl-3-isopropylcyclopentan 
• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 56326-41-1 Spiro-<4,5>-decenon (trans) 
• 74-88-4 methyl iodide 
• 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 
• 51174-45-9 5-chloro-3-methylpent-1-ene 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 5956-05-8 racem. 4-Epi-acorenon-B 

Downstream Products

• 5956-05-8 4-epi-acorenone 

Relevant academic research and scientific papers

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).

Spiroannelation via Intramolecular Ketocarbenoid Addition. Stereocontrolled Synthesis of (-)-Acorenone B and (+/-)-α-Chamigrene

The spirobicyclic structures of (+/-)-α-chamigrene (7) and (-)-acorenone B (6) were synthesized by means of a copper-catalyzed, intramolecular cycloaddition of diazo ketones 25 and 47, respectively.The former was prepared from 4-methyl-4-(p-methoxyphenyl)pentanoic acid (8) and the latter was obtained in optically active form from (R)-(+)-limonene (35).Reduction of 26 with lithium in ammonia gave 27, which was transformed to (+/-)-α-chamigrene (7) via olefin 30 and carbinol 32.The tricyclic ketone 53, from 47, was converted via olefin 55 to spiroketone 56.Interoduction of the conjugated olefin afforded (-)-acorenone B (6).Alternatively, 53 was reduced with lithium in ammonia to 54 and this, through a parallel sequence, was taken to (-)-4-epiacorenone B (67).