Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin.
[reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. carmen.carrenno@uam.es
Merino
Estíbaliz
E
Ribagorda
María
M
Somoza
Alvaro
A
Urbano
Antonio
A
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D006873:Hydroquinones / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010407:Penicillium / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D006873:Hydroquinones; D007659:Ketones; D013454:Sulfoxides; C096606:dihydroepiepoformin; C506854:epiepoformin