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Synthesis 1999; 1999(5): 769-774
DOI: 10.1055/s-1999-3458
DOI: 10.1055/s-1999-3458
paper
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A Convergent Synthesis of CGS23305, A Thromboxane Synthase Inhibitor
Further Information
Publication History
Publication Date:
31 December 1999 (online)
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A convergent synthesis of CGS23305 was discovered. The route to the pyridine aldehyde intermediate 5 was reduced from four to two steps. The pyridine aldehyde was converted to the key pyridine aldehyde ester intermediate 7 via Miachel Addition of the N,N-diethylenamine 6 to ethyl acrylate. A Wittig alkenation using the multifunctional moiety 19 completed the carbons keleteon assembly. Hydrogenation and hydrolysis afforded CGS23305 in 44% overall yield from 14 (6 steps).
convergent synthesis - pyridine - aldehydes - thromboxane inhibitor