Total Synthesis of Aspidosperma and Strychnos Alkaloids through Indole Dearomatization

Abstract

Monoterpenoid indole alkaloids are the major class of tryptamine‐derived alkaloids found in nature. Together with their structural complexity, this has attracted great interest from synthetic organic chemists. In this Review, the syntheses of Aspidosperma and Strychnos alkaloids through dearomatization of indoles are discussed.

Novel Pathway for the Synthesis of 20-Deethyltubifolidine

“…This kind of method has never been implemented in the synthesis of Strychnos alkaloids The complex structures of such Strychnos alkaloids generated a challenge thus the research on the total syntheses of these compounds has been in a constant attempt in the synthetic organic chemistry community [27,28].…”

Total Syntheses of Dihydroindole Aspidosperma Alkaloids: Reductive Interrupted Fischer Indolization Followed by Redox Diversification

“…Without rival in the field of total synthesis has been the sustained interest to devise synthetic routes to Aspidosperma alkaloids (e.g., the archetypal 1 in Figure 1 ). 1 Their important biological activities and stereochemically rich pentacyclic scaffolds have rendered these compounds attractive targets for synthetic programs. 2 Over the last few decades, various elegant and innovative synthetic approaches have been reported and many of these strategies have made profound contributions to modern organic synthesis.…”

Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions

“…As a result, this class of compounds has frequently served as a benchmark target for the development of innovative synthetic methods and strategies. [2] In particular, aspidospermanes have often provided inspiration for the synthetic community to devise efficient catalytic approaches that allow the stereoselective construction of quaternary carbon stereocenters (C-5 and C-12 in Figure 1). The emerging power of these asymmetric methods has not only enriched the aspidosperma chemistry, but also enabled the pursuit of concise synthetic strategies and collective synthesis of structurally related aspidosperma alkaloids.…”