Synthesis of Alkaloid GB 13

Structure of Alkaloid GB 13

C20H29NO2

Principal investigator	Lewis N. Mander
Publication year	2003
Synthesis type	Total
Number of steps	31 (linear)
References	J. Am. Chem. Soc. 2003, 125, 2400. J. Org. Chem. 1980, 45, 1722.

Part 1 of 1

intermediate structure

+

intermediate structure

Li

NH3, THF

-33 °C, 2.5 h, 75%

See the Birch Reduction

intermediate structure

H2SO4

Acetone, H2O

0 °C, 2 h, 80%

See the Friedel-Crafts Alkylation

intermediate structure

AcOH

H2O

Reflux, 16 h, 89%

intermediate structure

MeOCH2Cl, i-Pr2NEt, DMAP

CH2Cl2

0 °C to RT, 16 h, 97%

intermediate structure

HCO2Me, NaH

THF

0 °C, 17 h

See the Claisen Condensation

intermediate structure

NsN3, Et3N

MeCN

0 °C to RT, 2 h

intermediate structure

TMS2NH

hν

THF

RT, 6 h, 68% (3 steps)

See the Wolff Rearrangement

intermediate structure

Et3N, Cl3CCOCl

CH2Cl2

0 °C, 5 min, 98%

intermediate structure

intermediate structure

i-Pr2NLi , KOt-Bu
(PhSe)2

THF

0 °C, 100 min

intermediate structure

intermediate structure

H2O2

EtOAc, H2O, THF

0 °C, 2 h, 74% (2 steps)

intermediate structure

+

intermediate structure

Special reagent

110 °C, 3 d, 87%

See the Diels-Alder Reaction

intermediate structure

n-Bu4N+ F-

THF

0 °C, 60 min, 74%

intermediate structure

LiAlH4

Et2O, THF

-78 °C, 5 min, 94%

intermediate structure

MeOCH2Cl, i-Pr2NEt, DMAP

CH2Cl2

0 °C to RT, 16 h, 96%

intermediate structure

Li

EtOH, NH3, THF

-78 to -33 °C

See the Birch Reduction

intermediate structure

HCl

H2O, MeOH, THF

RT, 45 min, 55% (2 steps)

intermediate structure

LiAlH4

Et2O

0 °C, 30 min

intermediate structure

mCPBA

CH2Cl2, Buffer (pH = 6.5)

RT, 2 h

See the Prilezhaev Reaction

intermediate structure

NaHCO3, Dess-Martin Periodinane

CH2Cl2

RT, 2.5 h, 77% (3 steps)

See the Dess-Martin Oxidation

intermediate structure

NsNHNH2, Pyr

THF

-78 °C to RT, 9 h, 76%

See the Eschenmoser Fragmentation

intermediate structure

NH2OH.HCl

Pyr

95 °C, 4 h

intermediate structure

NaBH4, ZrCl4

THF

RT, 16 h

intermediate structure

Zn

AcOH, Et2O

RT, 4 h

intermediate structure

(CF3CO)2O, Pyr

CH2Cl2

RT, 3 h, 32% (4 steps)

intermediate structure

HCl

Acetone, H2O

50 °C, 16 h

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 4 h, 80% (2 steps)

See the Dess-Martin Oxidation

intermediate structure

MeOCH2Cl, i-Pr2NEt, DMAP

CH2Cl2

0 °C to RT, 16 h, 71%

intermediate structure

i-Pr2NLi
TMSCl

THF

-78 °C, 35 min

intermediate structure

Pd(OAc)2

DMSO, MeCN

RT, 16 h, 82% (2 steps)

See the Saegusa-Ito Oxidation

intermediate structure

K2CO3

H2O, MeOH

55 °C, 16 h

intermediate structure

HCl

Acetone, H2O

55 °C, 20 h, 37% (2 steps)

intermediate structure

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