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Longifolene

Chemical structure of Longifolene
Author Alex G. Fallis
Publication year 1990
Synthesis type Total synthesis
Number of steps 17 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure + Chemical structure
Pyrrolidine
Arrow head
MeOH
0 °C to RT, 4 h, 86 %
Chemical structure
MeLi
Arrow head
THF
-78 to 0 °C, 10 min, 65 %
Chemical structure + Chemical structure
COCl2
Arrow head
PhMe
0 °C

No yield reported.
Chemical structure
LiAlH4
Arrow head


No yield reported.
Chemical structure
MnO2
Arrow head
81 %
Chemical structure + Chemical structure
i-Pr2NLi, CdCl2
Arrow head
THF
-40 to 0 °C, 2.5 h, 73 %

See the Aldol Addition
Chemical structure
BF3.OEt2
Arrow head
MeOH
RT, 4 h, 83 %
Chemical structure
µW
Arrow head
PhMe
2.5 h, 97 %

See the Diels-Alder Reaction
Chemical structure
H2, Pd/C
2 atm
Arrow head
EtOAc
RT, 4 h, 99 %
Chemical structure
LiAlH4
Arrow head
Et2O
0 °C to RT, 4 h, 95 %
Chemical structure
Ac2O, Pyr
Arrow head
Et2O
0 °C, 6 h, 74 %
Chemical structure
PhOC(S)Cl, Pyr
Arrow head
CH2Cl2
RT
Chemical structure
n-Bu3SnH, AIBN
Arrow head
PhMe
110 °C, 4 h, 71 %

See the Barton-McCombie Reaction
Chemical structure
NaI, TMSCl, Et3N
Arrow head
CH2Cl2
RT, 60 min
Chemical structure
PhOC(S)Cl, Pyr
Arrow head
CH2Cl2
RT
Chemical structure
n-Bu3SnH, AIBN
Arrow head
PhMe
110 °C, 4 h, 50 % (3 steps)

See the Barton-McCombie Reaction
Chemical structure
Flow system
Arrow head
PhH
525 °C, 56 %
Chemical structure

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