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

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.

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ChemInform Abstract: Ultrasonically Induced Conjugate Addition of Iodides to Electron- Deficient Olefins and Its Application to the Synthesis of Side-Chain Analogs of the Hormone 1α,25-Dihydroxyvitamin D3.

ChemInform ◽

10.1002/chin.199321112 ◽

2010 ◽

Vol 24 (21) ◽

pp. no-no

Author(s):

J. P. SESTELO ◽

J. L. MASCARENAS ◽

L. CASTEDO ◽

A. MOURINO

Keyword(s):

Conjugate Addition ◽

Side Chain ◽

Dihydroxyvitamin D3

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Highly efficient sulfur-containing polymeric photoinitiators bearing side-chain benzophenone and coinitiator amine for photopolymerization

Journal of Photochemistry and Photobiology A Chemistry ◽

10.1016/j.jphotochem.2006.07.020 ◽

2007 ◽

Vol 186 (1) ◽

pp. 106-114 ◽

Cited By ~ 35

Author(s):

Hongyu Wang ◽

Jun Wei ◽

Xuesong Jiang ◽

Jie Yin

Keyword(s):

Side Chain ◽

Highly Efficient ◽

Sulfur Containing

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ChemInform Abstract: CONFORMATIONAL ANALYSIS. 36. PREFERRED CONFORMATIONS OF 5-SUBSTITUTED 1,3-DIOXANES WITH SULFUR-CONTAINING AND ETHER FUNCTIONS IN THE SIDE CHAIN

Chemischer Informationsdienst ◽

10.1002/chin.197741272 ◽

1977 ◽

Vol 8 (41) ◽

pp. no-no

Author(s):

E. L. ELIEL ◽

D. KANDASAMY ◽

R. C. SECHREST

Keyword(s):

Conformational Analysis ◽

Side Chain ◽

Sulfur Containing

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Organocatalytic Stereoselective 1,6-Addition of Thiolacetic Acids to Propargylic Indole Imine Methides: Access to Axially Chiral Sulfur-containing Tetrasubstituted Allenes

Organic Chemistry Frontiers ◽

10.1039/d1qo00394a ◽

2021 ◽

Author(s):

Ziyang Wang ◽

Xiao Lin ◽

Xuling Chen ◽

Pengfei Li ◽

Wenjun Li

Keyword(s):

Phosphoric Acid ◽

Conjugate Addition ◽

Chiral Phosphoric Acid ◽

Axially Chiral ◽

Propargylic Alcohol ◽

Acid Catalyzed ◽

Sulfur Containing ◽

Thiolacetic Acid

A chiral phosphoric acid catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to propargylic indole imine methide in situ formed from α-(3-indolyl) propargylic alcohol has been established, which enables the formation...

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