Total stereoselective synthesis of (+)-goniothalesdiol.
[reaction: see text] The stereoselective synthesis of (+)-goniothalesdiol (1) was accomplished in nine steps starting from commercially available (-)-(2S,3S)-dimethyl D-tartrate (3). The key features were a completely diastereoselective reduction of a beta-ketosulfoxide to generate the stereogenic center at C-5 in 7 and formation of the 2,5-cis-substituted tetrahydrofuran ring in 10 from a stereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization/deoxygenation.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. carmen.carrenno@uam.es
Hernández-Torres
Gloria
G
Urbano
Antonio
A
Colobert
Françoise
F
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry
C512389:(2S,3S)-dimethyl D-tartrate; D005663:Furans; D013644:Tartrates; C512388:goniothalesdiol