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Hirsutene

Chemical structure of Hirsutene
C15H24
Author Raymond L. Funk
Publication year 1984
Synthesis type Formal synthesis
Number of steps 8 (linear)
Reference

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Part 1 of 1
Chemical structure + Chemical structure
TiCl4
Arrow head
CH2Cl2
71 %

See the Hosomi-Sakurai Reaction
See the Michael Addition
Chemical structure
MeNHOH.HCl, NaOEt
Arrow head
PhMe, EtOH
Reflux, 24-36 h, 75 %

See the Huisgen Cycloaddition
Chemical structure
MeI
Arrow head
Chemical structure
H2, Pd
Arrow head
89 % (2 steps)
Chemical structure
mCPBA, NaHCO3
Arrow head
CH2Cl2, H2O
50 °C, 48 h, 90 %

See the Cope Elimination
Chemical structure
HCrO3Cl.Pyr
Arrow head
Chemical structure
H2, Pd
Arrow head
65 % (2 steps)
Chemical structure

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Arrow head
70 % (1 step)

See: Tetrahedron Lett. 1976, 17, 195.
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