Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigatorBarry B. Snider
Publication year1997
Synthesis typeTotal
Number of steps 7 (linear)
References
J. Org. Chem. 1997, 62, 1970.
Part 1 of 1
intermediate structure + intermediate structure
TMS2NLi
THF
-78 °C to RT, 2.5 h
intermediate structure intermediate structure
  1. NaH
  2. MeI
DME
-10 °C to RT, 8 h, 42% (2 steps)
"The yield was 56 % brsm (2 steps)."
intermediate structure
KH
1,3-Diaminopropane
RT, 3 h, 71%
See the Alkyne Zipper Reaction
intermediate structure
  1. i-Pr2NLi
  2. TMSCl
THF
-78 °C to RT, 3 h, 92%
intermediate structure
Mn(OAc)3.2H2O
AcOH, EtOH
90 °C, 22 h, 47%
"The yield was 62 % brsm."
intermediate structure
AcOH
100 °C, 5 h, 80%
intermediate structure
NaBH4
MeOH
0 °C, 60 min, 88%
intermediate structure
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