Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigator	George Büchi
Publication year	1979
Synthesis type	Total
Number of steps	10 (linear)
References	J. Am. Chem. Soc. 1979, 101, 6767.

Part 1 of 1

intermediate structure

mCPBA

CH2Cl2

See the Baeyer-Villiger Oxidation

intermediate structure

KOH

85% (2 steps)

intermediate structure

DDQ

MeOH

0 °C, 63%

intermediate structure

+

intermediate structure

SnCl4

CH2Cl2, MeNO2

-20 °C, 10 min

intermediate structure

+

intermediate structure

NaBH4

MeOH

-20 °C, 10 min, 10% (2 steps)

intermediate structure

Pd/C, H2

EtOAc

77%

intermediate structure

3,4-Dihydropyran, Camphorsulfonic acid

CH2Cl2

20 °C, 60 min

intermediate structure

Ca

NH3, THF

10 min, 78% (2 steps)

intermediate structure

Ph3P+CH3 Br-, n-BuLi

DMSO, THF

80 °C, 3.5 h

See the Wittig Reaction

intermediate structure

AcOH

H2O, THF

60 °C, 7 h, 78% (2 steps)

intermediate structure

Report an error in this part