Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigator	Alex G. Fallis
Publication year	1990
Synthesis type	Total
Number of steps	17 (linear)
References	J. Am. Chem. Soc. 1990, 112, 4609. Can. J. Chem. 1984, 62, 2451.

Part 1 of 1

intermediate structure

+

intermediate structure

Pyrrolidine

MeOH

0 °C to RT, 4 h, 86%

intermediate structure

MeLi

THF

-78 to 0 °C, 10 min, 65%

intermediate structure

+

intermediate structure

Phosgene

PhMe

0 °C

"No yield reported."

intermediate structure

LiAlH4

"No yield reported."

intermediate structure

MnO2

81%

intermediate structure

+

intermediate structure

i-Pr2NLi, CdCl2

THF

-40 to 0 °C, 2.5 h, 73%

See the Aldol Addition

intermediate structure

BF3.OEt2

MeOH

RT, 4 h, 83%

intermediate structure

µW

PhMe

2.5 h, 97%

See the Diels-Alder Reaction

intermediate structure

H2, Pd/C

2 atm

EtOAc

RT, 4 h, 99%

intermediate structure

LiAlH4

Et2O

0 °C to RT, 4 h, 95%

intermediate structure

Pyr, Ac2O

Et2O

0 °C, 6 h, 74%

intermediate structure

Pyr, PhOC(S)Cl

CH2Cl2

RT

intermediate structure

AIBN, n-Bu3SnH

PhMe

110 °C, 4 h, 71%

See the Barton-McCombie Reaction

intermediate structure

Et3N, TMSCl, NaI

CH2Cl2

RT, 60 min

intermediate structure

Pyr, PhOC(S)Cl

CH2Cl2

RT

intermediate structure

AIBN, n-Bu3SnH

PhMe

110 °C, 4 h, 50% (3 steps)

See the Barton-McCombie Reaction

intermediate structure

Flow system

PhH

525 °C, 56%

intermediate structure

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