Studies on oxidopyrylium [5+2] cycloadditions: toward a general synthetic route to the C12-hydroxydaphnetoxins.
[Structure: see text] 12-hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.
Wender
Paul A
PA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
Bi
F Christopher
FC
Buschmann
Nicole
N
Gosselin
Francis
F
Kan
Cindy
C
Kee
Jung-Min
JM
Ohmura
Hirofumi
H
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D015394:Molecular Structure
D001952:Bridged-Ring Compounds; D004224:Diterpenes