Synthesis of Upial

Structure of Upial

C15H20O3

Principal investigatorBarry B. Snider
Publication year1995
Synthesis typeFormal
Number of steps 10 (linear)
References
Tetrahedron 1995, 51, 12983.
Part 1 of 1
intermediate structure
  1. LDA
  2. (Z)-1-iodohex-3-ene
THF, DMPU
-78 °C to RT, 13 h, 54%
"Also isolated was the C6-epimer (9%)"
intermediate structure
HCl
H2O, THF
RT, 6 h, 91%
intermediate structure
Cu(OAc)2.H2O, Mn(OAc)3.2H2O
AcOH
RT, 2 h, 29%
intermediate structure
TBSOTf, Et3N
CH2Cl2
0 °C to RT, 3 h
intermediate structure
MeLi
THF
-78 °C, 1 h
intermediate structure
n-Bu4N+ F-
THF
RT, 10 min, 83% (3 steps)
intermediate structure
  1. NMO , OsO4
  2. KIO4
Acetone, H2O, t-BuOH
RT, 65 min, 89%
See the Lemieux-Johnson Oxidation
intermediate structure
2-Methyl-2-butene, NaClO2, NaH2PO4
H2O, t-BuOH
0 °C, 5 min
See the Pinnick-Lindgren Oxidation
intermediate structure
CH2N2
Et2O
RT, 93% (2 steps)
intermediate structure
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Remaining...
(4 steps)
"See : J. Am. Chem. Soc. 1985, 107, 5570"
intermediate structure