72165-33-4

Usage

InChI:InChI=1/C24H28O2/c1-18(2)8-7-9-19(3)12-15-22-23(25)16-21(17-24(22)26)14-13-20-10-5-4-6-11-20/h4-6,8,10-14,16-17,25-26H,7,9,15H2,1-3H3/b14-13+,19-12+

Upstream product

• 106-24-1 Geraniol 
• 22139-77-1 pinosylvin 
• 252679-37-1 4-((2E)-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl alcohol 
• 76280-59-6 methyl 3,5-bis(methoxymethoxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 1381781-06-1 C₂₂H₃₁BrO₄ 
• 1381781-05-0 C₂₂H₃₀Br₂O₄ 
• 495412-19-6 4-(3,7-dimethyl-octa-2,6-dienyl)-3,5-bis-methoxymethoxy-benzaldehyde 

Downstream Products

• 73436-06-3 amorphastilbol diacetyl ester 
• 98156-06-0 dihydroamorphastilbol dimethyl ether 
• 73436-03-0 2-geranyl-5-(2-phenylethyl)resorcin 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Meroterpenoid total synthesis: Conversion of geraniol and farnesol into amorphastilbol, grifolin and grifolic acid by dioxinone-β-keto-acylation, palladium catalyzed decarboxylative allylic rearrangement and aromatization

Biomimetic total syntheses of resorcinols amorphastilbol, grifolin and grifolic acid have been completed in four steps starting from geraniol and farnesol without the use of phenolic protection. The key steps involve C-acylation of dioxinone-β-keto esters, followed by palladium catalyzed decarboxylative allylic rearrangement and biomimetic aromatization.

Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives

Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.