Synthesis of Curvularin

Structure of Curvularin

C16H20O5

Principal investigator	Brian M. Stoltz
Publication year	2010
Synthesis type	Total
Number of steps	14 (3 parts)
References	Org. Lett. 2010, 12, 1612.. Org. Lett. 2010, 12, 1224.

Part 1 of 3

intermediate structure

Imidazole, TIPSCl

DMF

RT, 36 h, 41%

intermediate structure

BnBr, Cs2CO3

MeCN

RT

intermediate structure

n-Bu4N+ F-

THF

RT, 42% (2 steps)

intermediate structure

NBS

CH2Cl2

-78 °C, 90%

intermediate structure

TMS2NH

THF

70 °C, 5 h

intermediate structure

n-BuLi
Tf2O

-100 to -80 °C, 30 min, 74% (2 steps)

See the Brook Rearrangement

intermediate structure

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Part 2 of 3

intermediate structure

i-Pr2NLi
Acrolein

THF

-78 °C, 40 min, 76%

See the Aldol Addition

intermediate structure

TMSCl, TMS2NH

THF

70 °C, 5 h

intermediate structure

Grubbs-Hoveyda catalyst (3rd gen.)

PhH

Reflux, 20 h

See the Olefin Metathesis

intermediate structure

HCl

H2O, THF

RT, 2 h, 57% (2 steps)

intermediate structure

H2, Pd/C

1 atm

EtOH

RT

intermediate structure

Dess-Martin Periodinane

CH2Cl2

RT, 93% (2 steps)

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

CsF

MeCN

40 °C, 30%

intermediate structure

H2, Pd/C

1 atm

MeOH, THF

RT, 60%

intermediate structure

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