Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total 
Synthesis of Prostaglandin E2-1,15-Lactone

Fürstner, Alois; Grela, Karol

doi:10.1002/(SICI)1521-3773(20000403)39:7<1234::AID-ANIE1234>3.0.CO;2-V

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Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E₂-1,15-Lactone

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Grela, Karol
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Grela, K. (2000). Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E₂-1,15-Lactone. Angewandte Chemie International Edition, 39(7), 1234-1236. doi:10.1002/(SICI)1521-3773(20000403)39:7<1234:AID-ANIE1234>3.0.CO;2-V.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-3BFC-B

Abstract

The first total synthesis of a biologically relevant natural product (prostaglandin E₂-1,5-lactone; see picture) by ring-closing diyne metathesis followed by Lindlar reduction is reported. This conceptually novel strategy allows the stereoselective formation of macrocyclic Z alkenes which cannot be accessed stereoselectively by conventional ring-closing olefin metathesis.