90123-46-9Relevant articles and documents
IRIDOIDS: THE TOTAL SYNTHESIS OF THE AGLUCONES OF (+/-)-8-EPILOGANIN AND (+/-)-MUSSAENOSIDE VIA BICYCLOOCTENES
Storme, P.,Callant, P.,Vandewalle, M.
, p. 1019 - 1028 (2007/10/02)
The nitrone-olefin cycloaddition reaction has been used to construct cisfused bicyclooctanes or diquinanes as potential intermediates for C-11 functionalized iridoids.The isoxaolidine 7 was obtained in four steps from the commercially available 2-cyclopentene-1-acetic acid 4.Different functionalized diquinanes 8 to 19 and 22 to 24 have been prepared.As illustrative examples of iridoid synthesis, compounds 21 and 26, the O-methyl protected aglucones of (+/-)-8-epiloganin (2) and (+/-)-mussaenoside (3) have been synthesized starting from the common key-intermediate 11.