Efficient Synthesis of 1α-Fluoro A-Ring Phosphine Oxide, a Useful Building Block for Vitamin D Analogues, from (S)-Carvone via a Highly Selective Palladium-Catalyzed Isomerization of Dieneoxide to Dieneol

2001 ◽  
Vol 66 (18) ◽  
pp. 6141-6150 ◽  
Author(s):  
Marek M. Kabat ◽  
Lisa M. Garofalo ◽  
Andrzej R. Daniewski ◽  
Stanley D. Hutchings ◽  
Wen Liu ◽  
...  
Keyword(s):  
Vitamin D ◽  
Phosphine Oxide ◽  
Building Block ◽  
Efficient Synthesis ◽  
Vitamin D Analogues ◽  
Palladium Catalyzed

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

2002 ◽  
Vol 67 (11) ◽  
pp. 1658-1668 ◽  
Author(s):  
Agnieszka Przezdziecka ◽  
Alicja Kurek-Tyrlik ◽  
Jerzy Wicha
Keyword(s):  
Vitamin D ◽  
Butyl Ester ◽  
Acid Methyl Ester ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Vitamin D Analogues ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Organozinc Reagents

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

Design and efficient synthesis of novel vitamin D analogues bearing an aniline moiety in their side chains

2020 ◽  
Vol 61 (45) ◽  
pp. 152493
Author(s):  
Antonio Obelleiro ◽  
Uxía Gómez-Bouzó ◽  
Generosa Gómez ◽  
Yagamare Fall ◽  
Hugo Santalla
Keyword(s):  
Vitamin D ◽  
Side Chains ◽  
Efficient Synthesis ◽  
Vitamin D Analogues

Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D3and Analogues

2002 ◽  
Vol 67 (5) ◽  
pp. 1580-1587 ◽  
Author(s):  
Andrzej R. Daniewski ◽  
Lisa M. Garofalo ◽  
Stanley D. Hutchings ◽  
Marek M. Kabat ◽  
Wen Liu ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Building Block ◽  
Efficient Synthesis

ChemInform Abstract: Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D3 and Analogues.

ChemInform ◽  
2010 ◽  
Vol 33 (31) ◽  
pp. no-no
Author(s):  
Andrzej R. Daniewski ◽  
Lisa M. Garofalo ◽  
Stanley D. Hutchings ◽  
Marek M. Kabat ◽  
Wen Liu ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Vitamin D3 ◽  
Building Block ◽  
Efficient Synthesis
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