title: A concise stereocontrolled formal total synthesis of (+/-)-podophyllotoxin using sulfoxide chemistry.
abstract: A short stereoselective formal total synthesis of (+/-)-podophyllotoxin has been carried out from a sulfoxide, using a one-pot tandem conjugate addition/aldol/electrophilic aromatic substitution reaction to form a tetralin, which was converted into picropodophyllin in two steps.
authors.affiliation: Chemistry Department, the Centre for Synthesis and Chemical Biology, and the Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland. mike.casey@ucd.ie
authors.forename: Mike
authors.initials: M
authors.lastname: Casey
authors.forename: Claire M
authors.initials: CM
authors.lastname: Keaveney
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry
chemical_list: D013764:Tetrahydronaphthalenes; C415032:picropodophyllin; C095210:tetralin; D011034:Podophyllotoxin; D012451:Safrole; C005746:sulfoxide