Extension of hydrogen borrowing alkylation reactions for the total synthesis of (-)-γ-lycorane.
Christopher J J HallIndi S MarriottKirsten E ChristensenAaron J DayWilliam R F GoundryTimothy J DonohoePublished in: Chemical communications (Cambridge, England) (2022)
The total synthesis of (-)-γ-lycorane (10 steps) and synthesis of (±)-γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* (Me 5 C 6 ) deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project.