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Can I read Lessons from the total synthesis of (±)-phalarine: Insights into the mechanism of the Pictet–Spengler reaction on EtoBox?
Lessons from the total synthesis of (±)-phalarine: Insights into the mechanism of the Pictet–Spengler reaction by John D. Trzupek; Chaomin Li; Collin Chan; Brendan M. Crowley; Annekatrin C. Heimann; Samuel J. Danishefsky is a Chemistry article available to read on EtoBox.
What is Lessons from the total synthesis of (±)-phalarine: Insights into the mechanism of the Pictet–Spengler reaction about?
The furanobisindole alkaloid, phalarine, possesses a unique structural framework within the alkaloid family of natural products. Our laboratory recently disclosed the racemic total synthesis of phalarine, featuring an efficient azaspiroindolenine rearrangement; this achievement is revisited in detail. Upon completion of the first-generation total synthesis, we explored some interesting mechanism-level issues with regard to the key azaspiroindolenine rearrangement. These investigations provided valuable insights into the mechanism of racemization during the azaspiroindolenine rearrangement en route to synthetic phalarine. In addition, in the course of these studies, we demonstrated the Pictet–Spengler capture reaction for C~2~-aryl indoles, and successfully isolated the elusive azaspiroindolenine intermediate of the Pictet–Spengler reaction. Key insights into the remarkably subtle stereoelectronics that govern this rearrangement for C~2~-arylated indoles are discussed.
Who reads Lessons from the total synthesis of (±)-phalarine: Insights into the mechanism of the Pictet–Spengler reaction?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- John D. Trzupek; Chaomin Li; Collin Chan; Brendan M. Crowley; Annekatrin C. Heimann; Samuel J. Danishefsky
- Publisher
- International Union of Pure and Applied Chemistry; Walter de Gruyter GmbH; Wiley (ISSN 0033-4545)
- Published
- 2010
- Language
- EN
- Field
- Chemistry (Physical Sciences)