Total synthesis of (-)-SNF4435 C and (+)-SNF4435 D.
[reaction: see text] A convergent, biomimetic total synthesis of the immunosuppressant polyketides SNF4435 C and D is described. The synthetic pathway features a stereo- and regioselective [3,3]-sigmatropic rearrangement as well as a high-yielding Stille coupling/8pi-6pi electrocyclization cascade.
Beaudry
Christopher M
CM
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Trauner
Dirk
D
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009573:Nitrites / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009573:Nitrites; D009574:Nitro Compounds; D011753:Pyrones; C435067:SNF 4435C; C435066:SNF 4435D