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