A concise stereocontrolled formal total synthesis of (+/-)-podophyllotoxin using sulfoxide chemistry.
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.
Casey
Mike
M
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
Keaveney
Claire M
CM
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
D013764:Tetrahydronaphthalenes; C415032:picropodophyllin; C095210:tetralin; D011034:Podophyllotoxin; D012451:Safrole; C005746:sulfoxide