Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids: facile syntheses of biologically active terpenoids.
Regioselective halogenation of the terminal isopropylidene unit of different acyclic polyolefinic polyprenoids (farnesyl acetate, geranylgeranyl acetate, squalene, etc.) using NCS/catalytic polymer-supported selenenyl bromide is described; good to excellent yields are obtained (68-96%). The first applications of this protocol include the concise synthesis of bioactive terpenoids 1-3.
Barrero
Alejandro F
AF
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071, Granada, Spain. afbarre@goliat.ugr.es
Quílez Del Moral
José F
JF
Herrador
M Mar
MM
Cortés
Manuel
M
Arteaga
Pilar
P
Catalan
Julieta V
JV
Sanchez
Elena M
EM
Arteaga
Jesús F
JF
D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012643:Selenium / Q000737:chemistry*; D013185:Squalene / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D000498:Allyl Compounds; D006843:Hydrocarbons, Chlorinated; D013729:Terpenes; D013185:Squalene; D012643:Selenium