62023-90-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 4555, 1982 DOI: 10.1016/S0040-4039(00)85652-X

InChI:InChI=1/C18H18O2/c1-4-13-10(2)17(20)9-12-5-6-14-11(3)16(19)8-7-15(14)18(12)13/h4,7-9,19-20H,1,5-6H2,2-3H3

Upstream product

• 66447-86-7 juncusol dimethyl ether 
• 161424-41-5 9,10-dihydro-7-methoxy-3,8-dimethyl-4-(2-propenyl)-2-phenanthrenol acetate 
• 2987-06-6 4-(benzyloxy)cyclohexanone 
• 69496-44-2 2,7-dimethoxy-3,8-dimethyl-9,10-dihydrophenanthrene-4-carboxaldehyde 
• 17215-86-0 6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone 
• 91551-20-1 2,7-Dimethoxy-6-methoxymethyl-1-methyl-9,10-dihydro-phenanthrene 
• 91551-17-6 [(2,7-dimethoxy-8-methyl-9,10-dihydro-3-phenanthryl)methyl]dimethyl[(phenylthio)methyl]ammonium bromide 
• 85559-34-8 6-methoxy-5-methyl-1,2,3,4-tetrahydro-2-naphthalenol 
• 85559-30-4 4-(benzyloxy)-2-(methylthio)cyclohexanone 
• 85559-31-5 4-(benzyloxy)-2-(methylsulfinyl)cyclohexanone 
• 85559-32-6 6-Benzyloxy-1-methyl-5,6,7,8-tetrahydro-naphthalen-2-ol 
• 85559-33-7 2-(benzyloxy)-6-methoy-5-methyl-1,2,3,4-tetrahydronaphthalene 
• 85559-36-0 2,7-dimethoxy-3-(hydroxymethyl)-8-methyl-9,10-dihydrophenanthrene 
• 85559-37-1 3-(bromomethyl)-2,7-dimethoxy-8-methyl-9,10-dihydrophenanthrene 

Relevant academic research and scientific papers

Enynones in Organic Synthesis. 8. Synthesis of the Antimicrobial-Cytotoxic Agent Juncusol and Members of the Effusol Class of Phenols

Two new syntheses of phenols have been developed which have been utilized in an efficient preparation of the antimicrobial-cytotoxic agent juncusol (22) and several members of the effusol (23) class of phenols.These results complement our earlier studies with enynones of type 42 and provide for the highly efficient conversion of 42 to either methylenecyclopentenones 45 or phenols of type 47 or 54 with virtually 100percent selectivity.

A novel synthesis of juncusol

Juncusol (7) has been prepared by a novel electrocyclization process beginning with the known β-tetralone derivative 9.

Regiospecific Total Synthesis of Juncusol

A regiospecific, total synthesis of juncusol, a substituted 9,10-dihydrophenanthrene possessing antimicrobial and cytotoxic properties, based on two sequential aryl annulations is described.

REGIOSPECIFIC TOTAL SYNTHESIS OF JUNCUSOL

A regiospecific total synthesis of juncusol (1) based on the use of two consecutive phenol annulations is detailed.