Synthesis of Upial

Structure of Upial

C15H20O3

Principal investigatorMichael J. Taschner
Publication year1985
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure
Li, NH3, BrCH2CO2Et
t-BuOH
80%
"83:17 d.r.; major isomer shown"
intermediate structure
KOH
EtOH, H2O
intermediate structure
Li, NH3
EtOH
intermediate structure
TsOH
PhH
RT, , 53% (3 steps)
intermediate structure
MeI, LDA
THF
83%
intermediate structure
LiAlH4
Et2O
99%
intermediate structure
(COCl)2, DMSO, Et3N
99%
See the Swern Oxidation
intermediate structure
Ph3P=CHOMe
THF
71%
See the Wittig Reaction
intermediate structure
HCl
DME, H2O, THF
RT, , 70%
See the Aldol Addition
intermediate structure
MeMgBr
Et2O
0 °C, , 95%
intermediate structure
OsO4, NaIO4
75%
intermediate structure
KOCl
MeOH
0 °C, , 87 %
intermediate structure
(COCl)2, DMSO, Et3N
95%
See the Swern Oxidation
intermediate structure
Pyr, SOCl2
0 °C, , 82%
intermediate structure
HCl, NaBH3CN
AcOH, H2O, THF
75%
intermediate structure
  1. LDA
  2. PhCH=CHCH2Br
HMPA, THF
64%
intermediate structure
OsO4, NaIO4
70%
intermediate structure