Synthesis 2018; 50(04): 742-752
DOI: 10.1055/s-0036-1591735
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© Georg Thieme Verlag Stuttgart · New York

Complex Polycycles from Simple Propargyl Alcohols through Ruthenium-Catalyzed Cascade Reactions and One-Pot Procedures

Elisabeth Jäckel
Institute of Chemistry, Otto von Guericke University Magdeburg, Universitätsplatz 2, 39106 Magdeburg, Germany   Email: edgar.haak@ovgu.de
,
Julia Kaufmann
Institute of Chemistry, Otto von Guericke University Magdeburg, Universitätsplatz 2, 39106 Magdeburg, Germany   Email: edgar.haak@ovgu.de
,
Institute of Chemistry, Otto von Guericke University Magdeburg, Universitätsplatz 2, 39106 Magdeburg, Germany   Email: edgar.haak@ovgu.de
› Author Affiliations
This work was funded by the German Research Foundation DFG (HA 3554/7-1).
Further Information

Publication History

Received: 27 September 2017

Accepted: 07 November 2017

Publication Date:
29 November 2017 (online)

Abstract

Multiple bond-forming cascade transformations and one-pot procedures are valuable tools in organic synthesis and drug discovery. These atom-economical processes provide rapid access to natural product-like scaffolds from simple precursors. Herein, we report on ruthenium-catalyzed one-pot conversions of simple 1-alkenyl propargyl alcohols with cyclic 3-ketolactones and dienophiles. Thereby, structurally diverse fused polycycles and functionalized bicyclic structures are accessible from a common precursor with high selectivity. Some of the new drug-like molecules exhibit cytotoxic activity against KB cells.

Supporting Information

 
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