Synthesis of Upial

C15H20O3
Principal investigator | Barry B. Snider |
---|---|
Publication year | 1995 |
Synthesis type | Formal |
Number of steps | 10 (linear) |
References |
Part 1 of 1

- LDA
- (Z)-1-iodohex-3-ene
THF, DMPU
-78 °C to RT, 13 h, 54%
"Also isolated was the C6-epimer (9%)"

HCl
H2O, THF
RT, 6 h, 91%

Cu(OAc)2.H2O,
Mn(OAc)3.2H2O
AcOH
RT, 2 h, 29%

TBSOTf,
Et3N
CH2Cl2
0 °C to RT, 3 h

MeLi
THF
-78 °C, 1 h

n-Bu4N+ F-
THF
RT, 10 min, 83% (3 steps)



CH2N2
Et2O
RT, 93% (2 steps)

Remaining...
(4 steps)
"See : J. Am. Chem. Soc. 1985, 107, 5570"
