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ChemicalBook CAS DataBase List lantadene B
467-82-3

lantadene B synthesis

2synthesis methods
-

Yield:59157-82-3 98.9%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;methanol; for 0.0666667 h;Microwave irradiation;

Steps:

Microwave assisted reduction of Lantadene A and B

General procedure: The 100 mg (0.18 mM) of 1 and 2 were separately dissolved in 2 mL of methanol (1 mL) and tetrahydrofuran (1 mL).
To the reaction mixture, 6.80 mg (0.18 mM) of sodium borohydride was added and subjected for microwave irradiations at 210 W (30%) for 1-4 min.
The reaction was monitored on TLC after every 1 min and was incomplete up to 3 min and at 4 min reaction was completed to afford 3 and 4 respectively.
After completion of reactions dilute HCl solution was added to quench the unused NaBH4.
The organic solvents were evaporated in rota evaporator and precipitated reduced lantadenes were extracted with dichloromethane (DCM).
The solvent was removed under reduced pressure to give 3 (TLC, petroleum ether:ethyl acetate; 4:1, Rf 0.31) and 4, (TLC, petroleum ether:ethyl acetate; 4:1, Rf 0.28).
The product was recrystallized from methanol.

References:

Tailor, Navin K.;Boon, Hong L.;Sharma, Manu [European Journal of Medicinal Chemistry,2013,vol. 64,p. 285 - 291]

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