Unified total synthesis of pteriatoxins and their diastereomers.
A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.
Matsuura
Fumiyoshi
F
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Peters
René
R
Anada
Masahiro
M
Harried
Scott S
SS
Hao
Junliang
J
Kishi
Yoshito
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D049872:Bivalvia / Q000737:chemistry*; D002384:Catalysis; D008956:Models, Chemical; D009498:Neurotoxins / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D009498:Neurotoxins; D013141:Spiro Compounds