Synthesis of Okilactomycin

C24H32O6
Principal investigator | Amos B. Smith, III |
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Publication year | 2007 |
Synthesis type | Total |
Number of steps | 37 (3 parts) |
References |
Part 1 of 3
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BH3.NH3,
i-Pr2NLi
THF
0 °C to RT, 3 h, 94%



n-Bu4N+ F-
THF
0 °C to RT, 5 h, 97%




H2O2,
LiOH
H2O
0 °C to RT, 2 h, 97%

Part 2 of 3
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LiAlH4
Et2O
-78 °C to RT, 90 min, 97%


HF
MeCN
RT, 60 min, 90% (2 steps)

- Li(s-Bu)3BH
- PhNTf2
THF
-78 °C to RT, 7.5 h, 82%

Pd(PPh3)4,
LiCl,
CO,
n-Bu3SnH
THF
70 °C, 5 h, 87%


CH2Cl2
-78 °C, 60 min, 71%



- NaH
- n-Bu4N+ I- , 2-Bromomethylnaphthalene
DMF
0 °C to RT, 36 h, 96%
See the Williamson Ether Synthesis

- Cp2ZrHCl
- NBS
CH2Cl2
0 °C to RT, 40 min, 98%

PhSeH,
Cs2CO3
MeCN
RT, 60 min, 93%

Part 3 of 3
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TMSOTf,
i-PrOTMS
CH2Cl2
0 °C, 30 min




Pyr
CHCl3
RT to 60 °C, 2.5 h, 94%

DDQ
CH2Cl2, MeOH
RT, 60 min, 84%

- TMS2NK
- ClCO2Me
THF
-78 to 0 °C, 65 min, 99%

NaOMe
THF
0 °C, 60 min

K2CO3,
MeI
MeCN
70 °C, 2 h, 88% (2 steps)


Pd/C,
H2
1 atm
EtOAc
RT, 15 h, 84% (2 steps)


SeO2,
t-BuOOH
CH2Cl2
10 °C, 40 min, 54%
"The yield was 62 % brsm."

SOCl2,
Propylene oxide
Et2O
0 °C, 4 h, 74%

- TMS2NNa
- PhSeCl
THF
-78 °C, 30 min, 83%


NaIO4
H2O, THF
RT, 5 h, 90%

2-Methyl-2-butene,
NaH2PO4,
NaClO2
H2O, t-BuOH, THF
RT, 60 min, 80%
See the Pinnick-Lindgren Oxidation
