1606140-84-4Relevant academic research and scientific papers
Diversity-Oriented Approach to Normuscopyridine and Its Analogues through Ring-Closing Metathesis
Kotha, Sambasivarao,Waghule, Gopalkrushna T.,Shirbhate, Mukesh E.
, p. 984 - 992 (2014)
Ring-closing metathesis (RCM) is a useful protocol for assembling macrocycles. To synthesize normuscopyridine, and its analogues we used RCM as a key step in our strategy. Our approach to the synthesis of pyridine macrocycles involves two routes. The first approach starts with alkenylation of 2,6-bis[(phenylsulfonyl)methyl]pyridine and involves five steps with 10 % overall yield. The second route begins with Grignard addition to pyridine-2,6-dicarbo nitrile, followed by RCM and one-pot removal of the carbonyl group before hydrogenation of the double bond in 28 % overall yield. This approach has only three steps. Neither route involves the use of protecting groups. Various points of diversification are embedded in our strategy and eight different cyclophanes were assembled by adopting a general approach to these macrocyclics. Various derivatives of muscopyridine, which is an important constituent for the perfumery industry, were assembled through ring-closing metathesis and include points for diversification that allow for variation in chain length. Reduction of carbonyl and double bonds was successfully effected in one step. Neither route involves use of protecting groups. Eight different cyclophanes were assembled.
Diversity-oriented approach to normuscopyridine and its analogues through ring-closing metathesis
Kotha, Sambasivarao,Waghule, Gopalkrushna T.,Shirbhate, Mukesh E.
, p. 984 - 992 (2014/03/21)
Ring-closing metathesis (RCM) is a useful protocol for assembling macrocycles. To synthesize normuscopyridine, and its analogues we used RCM as a key step in our strategy. Our approach to the synthesis of pyridine macrocycles involves two routes. The first approach starts with alkenylation of 2,6-bis[(phenylsulfonyl)methyl]pyridine and involves five steps with 10 % overall yield. The second route begins with Grignard addition to pyridine-2,6-dicarbo nitrile, followed by RCM and one-pot removal of the carbonyl group before hydrogenation of the double bond in 28 % overall yield. This approach has only three steps. Neither route involves the use of protecting groups. Various points of diversification are embedded in our strategy and eight different cyclophanes were assembled by adopting a general approach to these macrocyclics. Various derivatives of muscopyridine, which is an important constituent for the perfumery industry, were assembled through ring-closing metathesis and include points for diversification that allow for variation in chain length. Reduction of carbonyl and double bonds was successfully effected in one step. Neither route involves use of protecting groups. Eight different cyclophanes were assembled. Copyright
