Synthesis of Hellannuol A

Structure of Hellannuol A

C15H22O3

Principal investigator	Erich L. Grimm
Publication year	1994
Synthesis type	Total
Number of steps	11 (linear)
References	Tetrahedron Lett. 1994, 35, 6847.

Part 1 of 1

intermediate structure

BnBr, NaOH

EtOH, H2O

Reflux, 5.5 h, 65%

intermediate structure

LiAlH4

THF

0 °C to Reflux, 3.5 h

intermediate structure

PBr3

Et2O

0 °C

intermediate structure

PhSO2Na

DMF

RT, 15 h, 85% (3 steps)

intermediate structure

Pd/C, H2

EtOAc

100%

intermediate structure

CHCl3, NaOH

Acetone

Reflux

See the Bargellini Reaction

intermediate structure

CH2N2

Et2O

70% (2 steps)

intermediate structure

TMS2NLi

THF

0 °C to RT, 90 min, 87%

intermediate structure

NaBH4

MeOH

0 °C, 90 min, 83%

intermediate structure

Na(Hg)

MeOH

0 °C to RT, 16 h, 45%

intermediate structure

NaSEt

DMF

150 °C, 16 h, 70%

intermediate structure

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