Efficient conversion of carbohydrates into 1-C-alditols: application to the synthesis of chiral gamma-substituted butenolides and bicyclic alkaloid analogues.
Readily available sugar derivatives were transformed in a few steps into valuable, more complex products. The tandem radical scission of carbohydrates-oxidation reaction gave acetoxy acetals, which were converted into a variety of chiral C-alditols in good global yields and excellent 1,2-trans stereoselectivity. The reaction was the key step in the synthesis of hydroxylated gamma-substituted butenolides and bicyclic alkaloid analogues.
Boto
Alicia
A
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain. alicia@ipna.csic.es
Hernández
Dácil
D
Hernández
Rosendo
R
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D004951:Esterification; D006900:Hydroxylation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000080:Acetals; D000470:Alkaloids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates; D007659:Ketones; C004511:butenolide; D015107:4-Butyrolactone