Synthesis of Preussin

Structure of Preussin

C21H35NO

Principal investigator	Nabin C. Barua
Publication year	2006
Synthesis type	Total
Number of steps	9 (linear)
References	Eur. J. Org. Chem. 2006, 1722.

Part 1 of 1

intermediate structure

AllylSnBu3, Ti(Oi-Pr)4, (S)-BINOL

CH2Cl2

-78 to -20 °C, 36 h, 82%

See the Keck Asymmetric Allylation

intermediate structure

I2, Ac2O

RT, 10 min, 92%

intermediate structure

NaIO4, OsO4, 2,6-Lutidine

Dioxane , H2O

RT, 30 min, 86%

See the Lemieux-Johnson Oxidation

intermediate structure

+

intermediate structure

La(Ot-Bu)3, (S)-BINOL

THF

-50 °C, 60 h, 73%

See the Henry Reaction

intermediate structure

Pd/C, H2

1 atm

MeOH

RT, 3 h, 90%

intermediate structure

HCl

H2O

RT, 2 h, 80%

intermediate structure

Boc2O, NaHCO3

EtOAc, H2O

RT, 3 h, 91%

intermediate structure

MsCl, Et3N

CH2Cl2

0 °C to RT, 6 h, 75%

intermediate structure

LiAlH4

THF

Reflux, 8 h, 60%

intermediate structure

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