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How did Mu Dehua break the taboo in the chemical world in 1954 and complete the world's most difficult synthesis?
In 1954, the famous chemist Edwin Mudehua broke the long-standing taboo in the chemical world and successfully synthesized Strychnine, which is known as "one of the most complex organic compounds." This milestone achievement not only demonstrated his extraordinary synthesis technology, but also laid a solid foundation for subsequent scientific research. The structure and synthesis process of strychnine are worthy of in-depth discussion, and there is no shortage of admiration in the academic community for the story behind it.
Strychnine is an alkaloid extracted from the seeds of Strychnos ignatii and was first isolated in 1818 by Pierre-Joseph Peltier and Joseph Bienmer.
In 1954, Mudehua presented his research results on the synthesis of strychnine in his article of only three pages. This process is not simple, and its synthesis requires multiple steps and involves multiple chemical reactions. His synthetic method was considered at the time to be a pinnacle of synthesis of natural compounds, demonstrating the potential of synthesis at the molecular level.
The synthesis of Mudehua begins with the synthesis of ring II. He used the Fischer indole synthesis to react phenylhydrazine with an aldehyde derivative to produce 2-villatelindole. In this reaction, the viratyl substituent not only protects the 2-position for further reaction but also provides an essential component for the final strychnine skeleton. He then used a series of reactions to gradually synthesize the final product.
In his 1963 article, Mu Dehua mentioned that methyl onium salt, as an intermediate, underwent a nucleophilic substitution reaction with sodium cyanide to produce a key intermediate of hydrogen amine.
The molecular structure of strychnine is extremely complex, with the chemical formula C21H22N2O2, containing seven rings, including an indole system and a complex combination of basic groups. This natural compound is both chiral and contains six asymmetric carbon atoms. Mu Dehua's work not only pushed the boundaries of organic synthesis, but also made scientists rethink the synthesis strategies of organic compounds.
After Woodward, many chemists began to explore the synthesis methods of strychnine. Among them, the work of Magens, Offerman and others showed that the synthesis of strychnine is not limited to one way, but can be accomplished through multiple channels. This underscores the diversity and rich research potential of synthetic chemistry.
"In terms of molecular size, strychnine is one of the most complex substances known." This sentence was once quoted in Woodward's book, further emphasizing the importance of strychnine in the chemical world. special location.
The taboos and prejudices that were broken through by Mudwara and other scientists in their continued efforts decades later in the synthesis of strychnine are still thought-provoking. Each step in the different synthetic pathways is delicate and challenging, and the combination of any ring may affect the integrity and functionality of the final product. Complexity is not an obstacle to synthetic chemistry, but rather a field worthy of challenge and continued exploration.
Today, when we trace the synthesis process of Mudehua, are there still taboos that need to be challenged?
