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TMS
Al(OiPr)3
3 steps
OH
Mechanism?
HO
1) SOCl2
2) NaH, nBuLi
O
O
OEt
Cl
EtOOC
Cl
Mn(OAc) 3
H
O
1) Zn, AcOH
2) MVK, tBuOK
MVK=
2 step identici
3 steps
EtOOC
H
TBSO
1) NaCN
2) Ac2O
TBSO
1 step
H
AcO
AcO
TBHP, CuBr
O
TBSO
TBSO
H
AcO
1) Dess-Martin
2) TBAF
Birch
H
O
H
HO
H
O