Synthesis of Muscone

Structure of Muscone

C16H30O

Principal investigatorWolfgang Oppolzer
Publication year1993
Synthesis typeTotal
Number of steps 7 (linear)
References
J. Am. Chem. Soc. 1993, 115, 1593.
Part 1 of 1
intermediate structure + intermediate structure
n-BuLi
HMPA, THF
-10 to 0 °C, 60 min, 98%
intermediate structure
Li, KOt-Bu
1,3-Diaminopropane
RT, 2 h, 93%
See the Alkyne Zipper Reaction
intermediate structure
Et3N, DMSO, (COCl)2
CH2Cl2
-78 °C to RT, 70 min, 95%
See the Swern Oxidation
intermediate structure
Special reagent
  1. Cy2BH
  2. Et2Zn
Hexane(s)
0 °C, 6 h, 75%
"96:04 e.r."
intermediate structure
ClCH2I, Et2Zn
DCE
0 °C, 40 min, 91%
See the Simmons-Smith Reaction
intermediate structure
Et3N, DMSO, (COCl)2
CH2Cl2
-78 °C to RT, 20 min, 98%
See the Swern Oxidation
intermediate structure
Li
Et2O, NH3
-78 °C, 60 min, 84%
intermediate structure
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