Synthesis of Clostrubin

Structure of Clostrubin

C25H18O6

Principal investigator	Ang Li
Publication year	2015
Synthesis type	Total
Number of steps	13 (3 parts)
References	Nat. Commun. 2015, 6, 6445.

Part 1 of 3

intermediate structure

+

intermediate structure

SiO2

THF

-78 °C to RT, 8 h

See the Diels-Alder Reaction

intermediate structure

K2CO3, MeI

DMF

RT, 18 h, 45% (2 steps)

See the Williamson Ether Synthesis

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HCl, SnCl2.2H2O

AcOH, H2O

RT, 30 min

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DBU, TsN3

CH2Cl2

RT, 20 h, 89% (2 steps)

intermediate structure

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Part 2 of 3

intermediate structure

(CH2O)n, Et3N, MgCl2

THF

Reflux, 84%

See the Casnati-Skattebøl Formylation

intermediate structure

MeI, K2CO3

DMF

RT, 24 h, 99%

See the Williamson Ether Synthesis

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MeMgBr
HMPA , TMSCl , Et3N

THF

0 °C to RT, 20 min, 94%

See the Grignard Reaction

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EtMgBr
CS2
MeI
H2O , HCl

THF

RT to 70 °C, 12 h, 67%

See the Grignard Reaction

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Dess-Martin Periodinane

CH2Cl2

RT, 1 min, 83%

See the Dess-Martin Oxidation

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NaOMe

MeOH

RT to 50 °C, 4 h, 66%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

Rh2(OAc)4
Cu

PhMe

50 to 110 °C, 2 h, 85%

See the Barton-Kellogg Reaction

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hv

CHCl3

RT, 8 h, 55%

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HBr

AcOH, H2O

120 °C, 10 h, 95%

intermediate structure

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