Synthesis of Cyclophellitol

Structure of Cyclophellitol

C7H12O5

Principal investigator	Ken-Ichi Sato
Publication year	1994
Synthesis type	Total
Number of steps	13 (linear)
References	Chem. Lett. 1994, 23, 37.

Part 1 of 1

intermediate structure

i-Pr2NLi

CH2Cl2, THF

-78 °C, 82%

intermediate structure

NaBH4

DMSO

80 °C, 82%

intermediate structure

Ac2O

Pyr

RT, 100%

intermediate structure

BaCO3, NBS

CCl4

Reflux

See the Hanessian-Hullar Reaction

intermediate structure

NaI

Acetone

Reflux

See the Finkelstein Reaction

intermediate structure

DBU

4 Å MS

DMSO

80 °C, 60 min, 56% (3 steps)

intermediate structure

HgCl2

Acetone, H2O

Reflux, 60 min

See the Petasis-Ferrier Rearrangement

intermediate structure

MsCl, Et3N

CH2Cl2

0 °C, 86% (2 steps)

intermediate structure

CeCl3.7H2O, NaBH4

CH2Cl2, EtOH

-78 °C, 67%

See the Luche Reduction

intermediate structure

TBSCl, Imidazole

DMF

40 °C, 94%

intermediate structure

KOH

EtOH

RT, 20 min, 80%

intermediate structure

mCPBA

DCE

40 °C, 24 h, 84%

See the Prilezhaev Reaction

intermediate structure

AcOH

H2O

RT, 60 min, 100%

intermediate structure

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