Now that you’ve reached the Island, it’s time to inspect the procedure! Move carefully to avoid the security system and prevent running from the guards! The last thing you want is Mrs.Incredible to be an experiment!
Experimental
Compound 39
To a solution of enone (600 mg, 1.5 mmol) in CH2Cl2, PhSH (190 mg, 1.2 eq) and triethylamine (30mg, 0.2 eq) was added at 0 degrees Celsius. 30 min later, the reaction temperature was cooled to -50 degrees Celsius and EtOh was injected at a 1:1 ratio with CH2Cl2. To this reaction mixture was added NaBH4 (200 mg, 6 eq) and reaction temperature was slowly warmed up to 0 degrees Celsius over the course of 2 hours. Acetone was added to quench the extra NaBH4. 20 min later water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over MgSO4. After filtration of the solid, the solvent was removed under reduced pressure. The residue was purified under flash chromatography in order to give compound 39 as a 1:1 ratio of C-16 epimers (597 mg, 78% yield) these two epimers could not be separated and characterized as a mixture.
To a solution of enone (600 mg, 1.5 mmol) in CH2Cl2, PhSH (190 mg, 1.2 eq) and triethylamine (30mg, 0.2 eq) was added at 0 degrees Celsius. 30 min later, the reaction temperature was cooled to -50 degrees Celsius and EtOh was injected at a 1:1 ratio with CH2Cl2. To this reaction mixture was added NaBH4 (200 mg, 6 eq) and reaction temperature was slowly warmed up to 0 degrees Celsius over the course of 2 hours. Acetone was added to quench the extra NaBH4. 20 min later water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over MgSO4. After filtration of the solid, the solvent was removed under reduced pressure. The residue was purified under flash chromatography in order to give compound 39 as a 1:1 ratio of C-16 epimers (597 mg, 78% yield) these two epimers could not be separated and characterized as a mixture.
Glossary
Drying: the removal of H2O or some other liquid through the use of a drying agent (for example MgSO4) which can bind to H20 and remove it from solution.
Extraction: the process of using two immiscible substances in order to extract a solute from one phase into another (i.e. drawing a solute in an aqueous face into an organic phase).
Flash Chromatography: A type of column chromatography in which a 0.1-10 g sample of mixture is separated in less than 15 min by using pressurized gas to drive the solvent through the column.
