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Search synthesis

Gymnomitrol

Chemical structure of Gymnomitrol
C15H24O
Author Barry B. Snider
Publication year 1997
Synthesis type Total synthesis
Number of steps 7 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
TMS2NLi
THF
-78 °C to RT, 2.5 h

Selectivity : 91:09
Chemical structure
+
Chemical structure
  1. NaH
  2. MeI
DME
-10 °C to RT, 8 h, 42% (2 steps)

The yield was 56 % brsm (2 steps).
Chemical structure
KH
1,3-Diaminopropane
RT, 3 h, 71%

See the Alkyne Zipper Reaction
Chemical structure
  1. i-Pr2NLi
  2. TMSCl
THF
-78 °C to RT, 3 h, 92%
Chemical structure
Mn(OAc)3.2H2O
EtOH, AcOH
90 °C, 22 h, 47%

Selectivity : 70:30
The yield was 62 % brsm.
Chemical structure
AcOH
100 °C, 5 h, 80%
Chemical structure
NaBH4
MeOH
0 °C, 60 min, 88%
Chemical structure

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