5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one: New 2H-Pyran-2-one Synthons
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (19) , 6693-6699
- https://doi.org/10.1021/jo951394t
Abstract
5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively. This reaction is applicable to the enol triflates of 14β-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.Keywords
This publication has 9 references indexed in Scilit:
- 3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditionsTetrahedron Letters, 1991
- A cycloaddition route to 14-hydroxysteroidsTetrahedron Letters, 1989
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexesJournal of Organometallic Chemistry, 1981
- Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)Proceedings of the National Academy of Sciences, 1978
- Poly(p-phenylene). The Reaction of 5,5'-p-Phenylenebis-2-pyrone with p-DiethynylbenzeneMacromolecules, 1972
- Preparation of Cyclic and Acyclic Vinyl TrifluoromethanesulfonatesAngewandte Chemie International Edition in English, 1970
- Synthesis of bufadienolides. Synthesis of bufalin and resibufogeninJournal of the American Chemical Society, 1969
- Vinyl Derivatives of the Metals. I. Synthesis of Vinyltin CompoundsJournal of the American Chemical Society, 1957