Synthesis of Luciduline

Structure of Luciduline

C13H21NO

Principal investigator	Wolfgang Oppolzer
Publication year	1976
Synthesis type	Total
Number of steps	7 (linear)
References	J. Am. Chem. Soc. 1976, 98, 6722.

Part 1 of 1

intermediate structure

+

intermediate structure

SnCl4

MeCN

RT, 24 h

See the Diels-Alder Reaction

intermediate structure

NaOAc, NH2OH.HCl

MeOH

40% (2 steps)

intermediate structure

NaBH3CN

MeOH

RT, 60 min, 100%

intermediate structure

(CH2O)n

Sealed tube

PhMe

115 °C, 14 h, 70%

See the Huisgen Cycloaddition

intermediate structure

MeOSO2F

Et2O

0 °C, 60 min

intermediate structure

LiAlH4

THF

RT, 5 h, 97% (2 steps)

intermediate structure

CrO3, H2SO4

Acetone, H2O

98%

See the Jones Oxidation

intermediate structure

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