One-step Synthesis for the Preparation of Quinoline Alkaloid Analogues

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1953-1955

  Zografos, Alexandros L ^a   Mitsos, Christos A ^a   Igglessi Markopoulou, Olga ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

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Indexed keywords

EID: 0000663750     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9911021     Document Type: Article

References (21)

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15. For review and preparation of silyl ketene acetals, see: (a) Rasmussen, K. J. Synthesis 1977, 91.
16. (b) Brownbridge, P. Synthesis 1983, 1.
17. (c) Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 44, 4311.
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21. General Procedure. In a solution of 7 or 8 (1.5 mmol) in anhydrous dichloromethane, silyl ketene acetal (1.5 mmol) was added. The mixture was stirred at room temperature under argon, after which titanium tetrachloride was added in a dropwise manner. Stirring continued for 3 h. The mixture was quenced by water and extracted with dichlomethane. The dichloromethane extracts were evaporated in vacuo, and the residue was purified by column chromatography (chloroform - methanol 5:0.15) to afford the desired product.