Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17

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Title:Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17
Creators:
Przezdziecka, Agnieszka
Kurek-Tyrlik, Alicja
Wicha, Jerzy
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 11, pp. 1658-1668
Uncontrolled Keywords:Vinyl iodides, Negishi cross-coupling, Steroids, Vitamins, Organozinc reagents, Palladium

Abstract

Palladium-catalyzed coupling of steroid 17-iodo-6β-methoxy-3α,5-cyclo-5α-androst-16-ene (<strong>4</strong>) 17-iodoandrosta-5,16-dien-3β-ol (<strong>5</strong>), and structurally similar (3a<i>S</i>,7<i>R</i>,7a<i>R</i>)-benzenesulfonyl-3-iodo-3a-methyl-3a,4,5,6,7,7a-hexahydro-1<i>H</i>-indene (<strong>6</strong>) with various arylzinc chlorides, which were generated from aryl bromides <strong>8</strong> [1-bromomethylbenzene (<strong>8a</strong>), <i>O</i>-(triethylsilyl-2-bromophenyl)propan-2-ol (<strong>8b</strong>), 2-(4-bromophenyl)propan-2-ol (<strong>8c</strong>), 4-bromobenzonitrile (<strong>8d</strong>), 4-bromobenzoic acid methyl ester (<strong>8e</strong>), 4-bromobenzoic acid <i>tert</i>-butyl ester (<strong>8f</strong>) and 3-bromopyridine (<strong>8g</strong>)] <i>via</i> aryllihium derivatives (the Negishi coupling) was examined. The respective cross-coupling products were obtained in good yields for all aryl bromides except of <strong>8c</strong> and <strong>8e</strong>. Building blocks for synthesis of certain vitamin D analogues have been prepared. <p>

Title:Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17
Creators:
Przezdziecka, Agnieszka
Kurek-Tyrlik, Alicja
Wicha, Jerzy
Uncontrolled Keywords:Vinyl iodides, Negishi cross-coupling, Steroids, Vitamins, Organozinc reagents, Palladium
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:67
Number:11
Page Range:pp. 1658-1668
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021658UNSPECIFIED
ID Code:2024
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Przezdziecka, Agnieszka; Kurek-Tyrlik, Alicja; Wicha, Jerzy (2002) Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17. Collection of Czechoslovak Chemical Communications, 67 (11). pp. 1658-1668. ISSN 0010-0765

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