Stereoselective synthesis of 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofurans from cyclohexadienediols.
The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures.
Brovetto
Margarita
M
Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157, Montevideo, Uruguay. mbrovett@fq.edu.uy
Seoane
Gustavo
G
D000143:Acids / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D053138:Cyclohexenes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
D000143:Acids; D000475:Alkenes; D053138:Cyclohexenes; D005663:Furans; D010100:Oxygen