558461-45-3Relevant academic research and scientific papers
Total synthesis of (-)-lithospermoside
Josien-Lefebvre, Delphine,Le Drian, Claude
, p. 661 - 672 (2007/10/03)
The total synthesis of the naturally occurring noncyanogenic cyanoglucoside (-)-lithospermoside (1) was achieved starting from optically pure oxatrinorbornenone (+)-2 in 12 steps and 10% overall yield. The key step of the synthesis, the glycosidation, turned out to be very sensitive to steric hindrance, and we had, therefore, to optimize the choice of the protection used for the two other OH functions of the aglycone. Finally, the desired β-D-glucoside 15 was obtained in a very good yield (72%) under Koenigs - Knorr-glycosidation conditions, closely related to those used for the total synthesis of (-)-bauhinin.
