20150516 MeO OMegousei/synthetic/mondai/zemi-toi/zemitoi… · 20150516 MeO OMe Cl Cl Cl Cl Me H H...
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F. A. Khan et al. Org. Biomol. Chem. 2015, 13, 2768. 20150516 OMe MeO Cl Cl Cl Cl Me H H 1) OsO 4 , NMO acetone/H 2 O, rt, 90% 2) BF 3 ·OEt 2 , toluene reflux, 46% Me Cl Cl Cl O Cl O 1) mCPBA, CH 2 Cl 2 rt, 87% 2) BF 3 ·OEt 2 , CH 3 CN reflux, 71% OMe MeO Cl Cl Cl Cl Me H H N H Me O B.-L. Wang, H.-T. Gao, W.-D. Z. Li* J. Org. Chem. 2015, ASAP DOI: 10.1021/acs.joc.5b00365 O O CHO HO HO O O O HO HO OH OH HO HO OH OH A B C 1) MeLi (1.0 eq.), THF, 0 °C 2) (COCl) 2 (1.0 eq.), DMSO (2.0 eq.) CH 2 Cl 2 , -78 °C; NEt 3 (4.0 eq.), -78 °C 92% for 2 steps CF 3 CO 3 H (6.0 eq.) Na 2 HPO 4 (25 eq.) CH 2 Cl 2 , 0 °C, 53% 1) 6N HCl, THF, rt 2) Ac 2 O (6.0 eq.) DMAP (0.1 eq.) Py, rt, 68% 3) Burgess reagent (3.0 eq.) benzene, 50 °C 4) NaOMe (5.0 eq.) MeOH, rt + D (58%) E (12%) S O O Et 3 N N CO 2 Me Burgess reagent for B4
Transcript of 20150516 MeO OMegousei/synthetic/mondai/zemi-toi/zemitoi… · 20150516 MeO OMe Cl Cl Cl Cl Me H H...
F. A. Khan et al. Org. Biomol. Chem. 2015, 13, 2768.
20150516
OMeMeO
Cl
Cl
Cl
Cl Me
HH
1) OsO4, NMOacetone/H2O, rt, 90%
2) BF3·OEt2, toluenereflux, 46%
Me
Cl
ClCl
OCl
O
1) mCPBA, CH2Cl2rt, 87%
2) BF3·OEt2, CH3CNreflux, 71%
OMeMeO
Cl
Cl
Cl
Cl Me
HH N
HMe
O
B.-L. Wang, H.-T. Gao, W.-D. Z. Li* J. Org. Chem. 2015, ASAPDOI: 10.1021/acs.joc.5b00365
O
O
CHO
HO
HO
O
OO
HO
HO
OH
OH
HO
HO
OH
OH
A
B
C
1) MeLi (1.0 eq.), THF, 0 °C
2) (COCl)2 (1.0 eq.), DMSO (2.0 eq.)CH2Cl2, -78 °C;NEt3 (4.0 eq.), -78 °C92% for 2 steps
CF3CO3H (6.0 eq.)Na2HPO4 (25 eq.)
CH2Cl2, 0 °C, 53%
1) 6N HCl, THF, rt
2) Ac2O (6.0 eq.)DMAP (0.1 eq.)Py, rt, 68%
3) Burgess reagent (3.0 eq.)benzene, 50 °C
4) NaOMe (5.0 eq.)MeOH, rt
+
D (58%) E (12%)
SO
OEt3N N CO2Me
Burgess reagent
for B4