- H O O Me Me A Hbr Acoh A Then Naoh Aq 26 Nh B Ac20 Pyridine Ch2cl2 Me O 27 R H 28 R Ac 51 Combined R 1 (103.32 KiB) Viewed 9 times
H O-- O= Me Me a. HBr/AcOH, A; then NaOH(aq) 26 NH b. Ac20, pyridine, CH2Cl2 Me o 27: R = H, 28: R = Ac (51% combined) R
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H O-- O= Me Me a. HBr/AcOH, A; then NaOH(aq) 26 NH b. Ac20, pyridine, CH2Cl2 Me o 27: R = H, 28: R = Ac (51% combined) R
H O-- O= Me Me a. HBr/AcOH, A; then NaOH(aq) 26 NH b. Ac20, pyridine, CH2Cl2 Me o 27: R = H, 28: R = Ac (51% combined) R H OAC Me 29 (28%) (not carried forward) d. H2, Pd/C (cat.), MeOH e. LiAlH4, THE c. KOA, Me OH AcOH, A (63% from 27 77% from 28, 3 steps) Me fo 30 OH Me g. TFA, f. H Me Over OH H OH 15 Meo Me OH OH H DMAP (polymer-bound), CH2Cl2 Me cochlearenine (11) (25%, 34% brsm) Me 12 (quant.) CDC13 ОН Over H OH H h. H2O2 OH Me Me OH он (50%) 'N - Et TFA H Et н paniculamine (13) N-Et-1a-OH-17-veratroyldictizine (12•TFA)