Synthesis of Thiarubrine A

Structure of Thiarubrine A

C13H8S2

Principal investigator	Masato Koreeda
Publication year	1994
Synthesis type	Total
Number of steps	8 (linear)
References	J. Am. Chem. Soc. 1994, 116, 10793.

Part 1 of 1

intermediate structure

+

intermediate structure

KOH

DMF

RT, 3.5 h, 87%

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 91%

See the Dess-Martin Oxidation

intermediate structure

CBr4, Ph3P

CH2Cl2

0 °C, 50 min, 89%

See the Corey-Fuchs Reaction

intermediate structure

n-BuLi
MeI
DMF , BF3.OEt2

THF

-78 °C to RT, 9.5 h

See the Corey-Fuchs Reaction

intermediate structure

CBr4, Ph3P

CH2Cl2

0 °C, 50 min, 34% (2 steps)

See the Corey-Fuchs Reaction

intermediate structure

n-BuLi

THF

-78 °C to RT, 9.5 h, 54%

See the Corey-Fuchs Reaction

intermediate structure

VinylBr, Pd(PPh3)4, Et3N, CuI

PhMe

RT, 4.5 h, 41%

See the Sonogashira Coupling

intermediate structure

I2, n-Bu4N+ F-

3Å MS

THF

RT, 3 h, 53%

intermediate structure

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