A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-alpha-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical proof of the absolute stereochemistry of biosynthetically important (+)-hygroline (2) and (+)-hygrine (3).
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A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-alpha-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical proof of the absolute stereochemistry of biosynthetically important (+)-hygroline (2) and (+)-hygrine (3).
View Article and Find Full Text PDFTotal synthesis of hygrolines and pseudohygrolines.
J Org Chem
November 2013
ETH Zürich , Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, HCI H405, Wolfgang-Pauli Str. 10, CH-8093 Zürich, Switzerland.
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.
View Article and Find Full Text PDFRegioselective and stereoselective copper(I)-promoted allylation and conjugate addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine.
J Org Chem
June 2010
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK.
Copper salts have been screened for transmetalation and electrophilic quench of N-tert-butoxycarbonyl-2-lithiopyrrolidine (N-Boc-2-lithiopyrrolidine) and N-Boc-2-lithiopiperidine, formed by deprotonation of N-Boc-pyrrolidine and N-Boc-piperidine, respectively. Transmetalation with zinc chloride then (lithium chloride solubilized) copper cyanide followed by allylation typically gives mixtures of regioisomers (S(N)2 and S(N)2' products), whereas transmetalation with copper iodide.TMEDA then allylation occurs regioselectively (S(N)2 mechanism).
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