Ultrasonically induced conjugate addition of iodides to electron-deficient olefins and its application to the synthesis of side-chain analogs of the hormone 1.alpha.,25-dihydroxyvitamin D3

1993 ◽  
Vol 58 (1) ◽  
pp. 118-123 ◽  
Author(s):  
Jose Perez Sestelo ◽  
Jose L. Mascarenas ◽  
Luis Castedo ◽  
Antonio Mourino
Keyword(s):  
Conjugate Addition ◽  
Side Chain ◽  
Dihydroxyvitamin D3

Organometallics in prostaglandin synthesis

1988 ◽  
Vol 326 (1592) ◽  
pp. 579-585 ◽  
Keyword(s):  
Conjugate Addition ◽  
Prostaglandin Synthesis ◽  
Side Chain ◽  
Prostaglandin E ◽  
Controlled Synthesis ◽  
One Pot ◽  
Naturally Occurring ◽  
Chain Unit ◽  
Alkyl Iodides

An extremely short way to prostaglandins has been opened by combining the newly devised organometallic methodologies. Convergent, one-pot creation of the prostanoid framework is achieved by organocopper conjugate addition of the S-configurated ω-side-chain unit to (R)-4-trialkylsiloxy-2-cyclopentenone followed by the organotin-aided trapping of the enolate intermediate by α-side-chain alkyl iodides. Prostaglandin E 2 can be prepared in only three steps from the chiral building units. The protected 5,6-didehydro-PGE 2 derivatives thus obtained serve as common intermediates for the synthesis of a variety of naturally occurring prostaglandins including prostacyclin. This approach is also useful for the controlled synthesis of isocarbacyclin.

Synthesis of Side-Chain Locked Analogs of 1α,25-Dihydroxyvitamin D3 Bearing a C17 Methyl Group

2018 ◽  
Vol 20 (9) ◽  
pp. 2641-2644 ◽  
Author(s):  
Rita Sigüeiro ◽  
Miguel A. Maestro ◽  
Antonio Mouriño
Keyword(s):  
Side Chain ◽  
Dihydroxyvitamin D3 ◽  
Methyl Group

Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity

2002 ◽  
Vol 12 (22) ◽  
pp. 3255-3258 ◽  
Author(s):  
Yoshitomo Suhara ◽  
Atsushi Kittaka ◽  
Seishi Kishimoto ◽  
Martin J. Calverley ◽  
Toshie Fujishima ◽  
...  
Keyword(s):  
Cell Differentiation ◽  
Side Chain ◽  
Dihydroxyvitamin D3 ◽  
Marked Cell

Studies of vitamin D (calciferol) and its analogs. 43. Two novel allenic side chain analogs of 1.alpha.,25-dihydroxyvitamin D3

1992 ◽  
Vol 57 (16) ◽  
pp. 4374-4380 ◽  
Author(s):  
Andrew S. Craig ◽  
Anthony W. Norman ◽  
William H. Okamura
Keyword(s):  
Vitamin D ◽  
Side Chain ◽  
Dihydroxyvitamin D3

Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation

2017 ◽  
Vol 7 (1) ◽  
pp. 128-132 ◽  
Author(s):  
Jian-Ping Li ◽  
Hao-Ran Tuo ◽  
Ming-Sheng Xie ◽  
Bo Kang ◽  
Gui-Rong Qu ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Side Chain ◽  
Pyrimidine Nucleosides ◽  
Sulfur Containing
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