Collect. Czech. Chem. Commun. 2000, 65, 434-454

3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes

Miroslav Havránek and Dalimil Dvořák*

Department of Organic Chemistry, Prague Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic


Repeated Stille coupling of 3-substituted 3-(tributylstannyl)allyl alcohols 2 on a solid support was used to synthesize a 21 × 21 library of skipped dienes and a 21 × 21 × 21 library of skipped trienes. Starting 3-(tributylstannyl)allyl alcohols were prepared by Pd-catalyzed hydrostannation of substituted prop-2-yn-1-ols, by hydroalumination by LiAlH4 followed with transmetallation to tin using tributyltin methoxide, or by substitution of chlorine in (Z)-6-chloro-3-(tributylstannyl)hex-2-en-1-ol with appropriate nucleophile. Synthesized libraries were tested for the activity to endorphin receptors, but with negative results.

Keywords: Combinatorial chemistry; Libraries of structures; Stille coupling; Stannanes; Cross-coupling reactions; Solid-phase synthesis; Hydroalumination.

References: 24 live references.