`
`R\ SO,0R
`
`n Zs n (ey
`-n Heo=cH)\
`/
`
`R\ SO,OR
`
`R'=H or SO,OR
`MRAP R= CCalkyl
`
`x
`
`R\ SO,0R
`
`R\, SO20H
`
`prenhackn
`HOolpolarsolvent
`frenhack R' = H orSOOH
`
`x
`
`xX
`
`n
`
`Figure 1
`
`we
`
`0
`O=S=0
`|
`
`1.1.1 eq. LDA, THF, -78 °C
`°
`2. AaB ,0°C
`
`3.1.1eq. LDA, THF,-78°C
`4.
`
`,0°COaBr
`
`o7™
`_ | _
`O=S=0
`My MS
`30% Yield
`
`~~
`
`Figure 2
`
`
`
`eee
`
`Wilkinson's Catalyst
`H>, 600 psi
`toluene
`
`Figure 3
`
`ONa*
`NaOH
`aol
`
`DMSO, 50 °C
`
`x
`
`Figure 4
`
`
`
`one
`
`
`
` p
`
`po
`=o “<p
`ss
`Ng
`NS
`Ng
`Son O‘on O Yon O ‘on O ‘OH
`
`QOH LOH OOH OPH O,OH OOH
`
`x Sy So
`SoSdero
`
`
`
`
`ooo roroy o‘on‘OH 3,Xu
`
`KeJ
`N‘ .
`
`on Acid Channel
`
`p
`si
`a
`si
`GO ‘on © ‘on 0 ‘ou
`
`0, DH 9, OH
`OO
`
`sole
`
`Figure 5
`
`