Synthesis of Paeoniflorigenin

Structure of Paeoniflorigenin

C17H18O6

Principal investigator	Elias J. Corey
Publication year	1993
Synthesis type	Total
Number of steps	13 (linear)
References	J. Am. Chem. Soc. 1993, 115, 8871.

Part 1 of 1

intermediate structure

+

intermediate structure

KOAc, Mn3O(OAc)7

MeCN

RT, 90 min, 48%

intermediate structure

TfCl, Et3N

CH2Cl2

0 °C, 10 min, 70%

intermediate structure

NaHCO3, mCPBA

CH2Cl2

RT, 15 h, 81%

See the Prilezhaev Reaction

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 30 min, 78%

intermediate structure

TMSOTf

CH2Cl2

-78 °C, 60 min, 35%

intermediate structure

HCrO3Cl.Pyr

4 Å MS

CH2Cl2

RT, 30 min, 100%

intermediate structure

SmI2

THF

-45 °C, 10 h, 90%

intermediate structure

TMSCN

CH2Cl2

RT, 15 h, 82%

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 30 min, 86%

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 60 min, 81%

intermediate structure

Pyr, BzCl

CH2Cl2

RT, 3 h, 96%

intermediate structure

HCl

THF

0 °C, 6 h, 100%

intermediate structure

HF

MeCN

RT, 2 h, 91%

intermediate structure

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