Total synthesis of GEX1A.
An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 ( 1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.
Murray
Timothy J
TJ
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210-1185, USA.
Forsyth
Craig J
CJ
D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D005233:Fatty Alcohols; D007783:Lactones; D009942:Organometallic Compounds; D011714:Pyrans; C076087:herboxidiene; D012428:Ruthenium