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Named reactions

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Hirsutene

Chemical structure of Hirsutene
C15H24
Author Steven V. Ley
Publication year 1982
Synthesis type Total synthesis
Number of steps 12 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
KOt-Bu, n-BuLi
THF, HMPA
-78 °C, 80 min
Chemical structure
LiAlH4
Et2O
0 °C to RT, 60 min, 86% (2 steps)
Chemical structure
Br2, Ph3P
PhH, DMF
RT, 4 h, 59%

See the Appel Reaction
Chemical structure

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Part 2 of 3
Chemical structure
PhSeCl
Pyr
0 °C to RT, 105 min, 100%
Chemical structure
H2O2
CH2Cl2, H2O
0 °C to RT, 60 min, 96%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Mg, CuBr.Me2S
THF
-50 °C to RT, 80 min, 58%

See the Michael Addition
Chemical structure
N-(Phenylselenyl)phthalimide, SnCl4
CH2Cl2
0 °C to RT, 2.5 h, 45%
Chemical structure
Ni (Raney)
EtOH
50 °C, 2 h, 91%
Chemical structure
i-Pr2NLi, LiAlH4
THF
-78 to -20 °C, 2.5 h, 66%
Chemical structure
N-(Phenylselenyl)phthalimide, n-Bu3P
THF
RT, 2 h, 62%
Chemical structure
Ni (Raney)
EtOH
45 °C, 20 min, 83%
Chemical structure
CH2Br2, Zn, TiCl4
THF, CH2Cl2
-40 to 0 °C, 20 h, 98%

See the Lombardo Methylenation
Chemical structure

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