Synthesis of Taiwaniaquinol B

Structure of Taiwaniaquinol B

C20H28O4

Principal investigator	Dirk Trauner
Publication year	2006
Synthesis type	Total
Number of steps	6 (linear)
References	J. Am. Chem. Soc. 2006, 128, 11022.

Part 1 of 1

intermediate structure

NBS

DMF

RT, 42 h, 98%

intermediate structure

+

intermediate structure

n-BuLi

Et2O

-25 °C to RT, 105 min, 89%

intermediate structure

Dess-Martin Periodinane

CH2Cl2, Pyr

RT, 5 min, 90%

See the Dess-Martin Oxidation

intermediate structure

TMSOTf

MeNO2

105 °C, 65 min, 70%

See the Nazarov Cyclization Reaction

intermediate structure

BCl3

CH2Cl2

0 °C, 15 min, 90%

intermediate structure

(NH4)2Ce(NO3)6, Na2S2O4

CH2Cl2, H2O, MeCN

0 °C, 4 h, 51%

intermediate structure

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