The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D.
The size and positioning of substituents on a tetraene, along with the Woodward-Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8pi/6pi electrocyclization cascade. A biomimetic synthesis of (-)-SNF4435 C and (+)-SNF4435 D exploits these steric effects and allows confirmation of the predicted absolute stereochemistry of the natural products.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stoney Brook, New York 11794-3400, USA. kparker@notes.cc.sunysb.edu
Lim
Yeon-Hee
YH
D007166:Immunosuppressive Agents / Q000138:chemical synthesis; D009574:Nitro Compounds / Q000138:chemical synthesis*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D007166:Immunosuppressive Agents; D009574:Nitro Compounds; D011753:Pyrones; C435067:SNF 4435C; C435066:SNF 4435D