Synthesis of Preussin

Structure of Preussin

C21H35NO

Principal investigator	Won-Hun Ham
Publication year	2000
Synthesis type	Total
Number of steps	10 (linear)
References	Org. Lett. 2000, 2, 4041.

Part 1 of 1

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 2 h

See the Dess-Martin Oxidation

intermediate structure

VinylMgBr

THF

0 °C, 70% (2 steps)

See the Grignard Reaction

intermediate structure

Ac2O, Pyr

CH2Cl2

RT, 99%

intermediate structure

K2CO3, Pd(PPh3)4

MeCN

Reflux, 83%

See the Tsuji-Trost Reaction

intermediate structure

9-BBN
H2O , H2O2

THF

82%

intermediate structure

RuCl3, NaIO4, NaHCO3

CCl4, H2O, MeCN

intermediate structure

DCC, DMAP, NHMeOMe.HCl

CH2Cl2, Et3N

0 °C to RT, 12 h, 80% (2 steps)

intermediate structure

n-C9H19MgBr

THF

-30 to 0 °C, 60 min, 80%

See the Weinreb Ketone Synthesis

intermediate structure

H2, Pd(OH)2/C

4.5 atm

AcOH, MeOH

RT, 24 h, 50%

intermediate structure

CH2O, NaBH3CN

AcOH, H2O, MeCN

20 °C, 4 h, 78%

intermediate structure

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