title: Total synthesis of sinenside A.
abstract: The first total synthesis of norlignan glucoside sinenside A has been accomplished. An intramolecular acetalization reaction has been employed as the key skeletal construct to forge the central cyclic disaccharide core. The trans-1,2-diol configuration present in the cyclic disaccharide of this natural product is unique and has been addressed by setting this configuration at the beginning. A 1,2-orthoester group has been selected as a handle for both sp glycosidation and for differentiation of the C2'-OH (that participates in the key acetalization reaction) of the sugar unit.
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. HomiBhabha Road, Pune 411008, India.
authors.forename: Paresh M
authors.initials: PM
authors.lastname: Vadhadiya
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. HomiBhabha Road, Pune 411008, India.
authors.forename: Chepuri V
authors.initials: CV
authors.lastname: Ramana
mesh_terms: D002241:Carbohydrates; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D005960:Glucosides; D017705:Lignans; C000602108:sinenside A