Synthesis of Ampelopsin F

Structure of Ampelopsin F

C28H22O6

Principal investigator	Scott A. Snyder
Publication year	2007
Synthesis type	Total
Number of steps	12 (linear)
References	Angew. Chem. Int. Ed. 2007, 46, 8186.

Part 1 of 1

intermediate structure

NaBH4

MeOH

0 °C, 30 min

intermediate structure

PBr3, Pyr

Et2O

40 °C, 3 h, 93% (2 steps)

intermediate structure

NBS

CH2Cl2

0 °C, 60 min, 95%

intermediate structure

HP(O)(OEt)2, TMS2NK

THF

0 °C to RT, 12.5 h, 91%

intermediate structure

+

intermediate structure

KOt-Bu

THF

-78 °C to RT, 13.5 h, 98%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

+

intermediate structure

n-BuLi

THF

-78 °C to RT, 5.5 h, 71%

intermediate structure

+

intermediate structure

TsOH

CH2Cl2

-50 °C to RT, 17.5 h, 65%

See the Prins Reaction

intermediate structure

NaHCO3, mCPBA

CH2Cl2

0 °C to RT, 3 h, 78%

intermediate structure

KOH

CCl4, H2O, t-BuOH

80 °C, 12 h, 52%

See the Ramberg-Bäcklund Reaction

intermediate structure

Br2

CH2Cl2

-78 °C to RT, 4 h, 53%

See the Friedel-Crafts Alkylation

intermediate structure

TMS3SiH, AIBN

PhMe

100 °C, 8 h, 89%

intermediate structure

BBr3

CH2Cl2

0 °C to RT, 19 h, 90%

intermediate structure

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