Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensin.
Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from d-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.
Prasad
Kavirayani R
KR
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. prasad@orgchem.iisc.ernet.in
Gholap
Shivajirao L
SL
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010208:Papaverine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
D005663:Furans; D007783:Lactones; D011753:Pyrones; D013343:Styrenes; C459359:altholactone; C527309:etharvensin; C080434:goniopypyrone; C073080:7-goniofufurone; C007639:ethaverine; C062903:goniotriol; D010208:Papaverine