Synthesis of Modhephene

Structure of Modhephene

C13H18O

Principal investigatorViresh H. Rawal
Publication year1997
Synthesis typeTotal
Number of steps 10 (linear)
References
Chem. Commun. 1997, 2381.
Part 1 of 1
intermediate structure
  1. i-Pr2NLi
  2. 4-Bromobut-1-ene
THF, DMPU
intermediate structure
  1. Dimsyl lithium
  2. Zn , NaOH , H2O
PhMe, THF
94% (2 steps)
intermediate structure
hν
PhH
89%
See the Paterno-Büchi Reaction
intermediate structure
LiDBB, AlMe3
THF
-78 °C to RT, 16 h, 86%
intermediate structure
H2Cr2O7.2Pyr
DMF
RT, 16 h, 91%
intermediate structure
  1. i-Pr2NLi
  2. PhSeCl
THF
-78 °C to RT, 61%
intermediate structure
n-Bu3SnH, AIBN
PhH
Reflux, 63%
"Also isolated was the C2-epimer (32 % yield)."
intermediate structure
BF3.OEt2, CuCN, MeLi
THF
See the Michael Addition
intermediate structure
Ph3P=CH2
THF
85% (2 steps)
See the Wittig Reaction
intermediate structure
TsOH
CH2Cl2
3 h, 100%
intermediate structure
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