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A ring-closing metathesis converts this compound into the eight-membered heterocycle 11, which is further processed to yield azidoalcohol 13. In the key step, this compound is transformed into the bicyclic pyrrolizidine 14. Establishment of the oxygen bridge then yields an azide (16), a branching point of the synthesis. b, Azide 16 can be converted to temuline 2 by reduction of the azide. Alternatively, reduction of the azide in the presence of di-tert-butyldicarbonate gives the N-Boc protected compound, which can be further transformed into N-methyl compound loline 1 and N-formyl loline.