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Updated: May 7, 2026
Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
Published on: April 8, 2020
Total synthesis of hygrolines and pseudohygrolines
Marc Liniger1, Katja Estermann, Karl-Heinz Altmann
1ETH Zürich , Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, HCI H405, Wolfgang-Pauli Str. 10, CH-8093 Zürich, Switzerland.
Abstract:
A concise two-step synthesis of all four diastereoisomeric hygrolines ((-)-hygroline (1), (+)-hygroline (2), (-)-pseudohygroline (3), (+)-pseudohygroline (4)) has been developed based on the (-)-sparteine (5)- or (+)-sparteine surrogate 11-mediated enantioselective lithiation of N-Boc pyrrolidine (6), followed by reaction of the chiral anion with (S)- or (R)-propylene oxide. Reduction of the resulting N-Boc amino alcohols furnished hygrolines and pseudohygrolines in 30% to 56% overall yields with dr's > 95:5.
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