Building a small polypropionate library. Synthesis of all possible stereotetrads (building blocks for polyketide synthesis) from furan.
The all diastereomeric stereotetrads (polypropionate fragments) were synthesized in a stereodivergent fashion, starting from the Diels-Alder adducts of furan with acrylic acid and (-)-2-camphanoxyacrylonitrile, respectively. The key intermediates of these sequences were the oxanorbornenic sulfones 7, (-)-53 and (+)-54. Regio- and stereocontrolled alkylative ring opening of these intermediates afforded the cyclohexenyl sulfones 14, (+)-55 and (-)-58 which were transformed into the desired stereotetrads 30, 31, 40, 41, (+)-62, (+)-63, (-)-66, and (+)-69.
Arjona
O
O
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense 28040-Madrid, Spain. plumety@eucmax.sim.ucm.es
Menchaca
R
R
Plumet
J
J
D000179:Acrylates / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis; D011422:Propionates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000179:Acrylates; D005663:Furans; D011108:Polymers; D011422:Propionates; C036658:acrylic acid; C039281:furan