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

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Title:3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes
Creators:
Havránek, Miroslav
Dvořák, Dalimil
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 3, pp. 434-454
Uncontrolled Keywords:Hydroalumination, Libraries of structures, Combinatorial chemistry, Solid-phase synthesis, Stannanes, Cross-coupling reactions, Stille coupling

Abstract

Repeated Stille coupling of 3-substituted 3-(tributylstannyl)allyl alcohols <strong>2</strong> 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 LiAlH<sub>4</sub> followed with transmetallation to tin using tributyltin methoxide, or by substitution of chlorine in (<i>Z</i>)-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. <p>

Title:3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes
Creators:
Havránek, Miroslav
Dvořák, Dalimil
Uncontrolled Keywords:Hydroalumination, Libraries of structures, Combinatorial chemistry, Solid-phase synthesis, Stannanes, Cross-coupling reactions, Stille coupling
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:3
Page Range:pp. 434-454
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000434UNSPECIFIED
ID Code:1653
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Havránek, Miroslav; Dvořák, Dalimil (2000) 3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes. Collection of Czechoslovak Chemical Communications, 65 (3). pp. 434-454. ISSN 0010-0765

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