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- Title
Rapid Generation of Molecular Complexity by Chemical Synthesis: Highly Efficient Total Synthesis of Hexacyclic Alkaloid (−)‐Chaetominine and Its Biosynthetic Implications.
- Authors
Geng, Hui; Huang, Pei‐Qiang
- Abstract
The efficiency becomes a key issue in today's natural product total synthesis. While biomimetic synthesis is one of the most elegant strategies to achieve synthetic efficiency and thus to approach the ideal synthesis, most biogenetic pathways are unknown or unconfirmed. In this account, we demonstrate, through the shortest and also the most efficient asymmetric total syntheses of the hexacyclic alkaloid (−)‐chaetominine to date, that on the basis of biogenetic thinking, one can develop quite efficient bio‐inspired total synthesis, which in turn serves to suggest and chemically validate plausible biosynthetic routes for the natural product. The synthetic strategy thus developed is also inspiring for the development of other synthetic methods and efficient total synthesis of other natural products. With biogenetic thinking, the hexacy‐clic alkaloid (−)‐chaetominine has been synthesized in only four steps from d‐tryptophan and in just five steps from L‐tryptophan. This short‐step generation of molecular complexity by chemical synthesis established several records in terms of steps, overall yields, and starting point.
- Subjects
CHEMICAL synthesis; NATURAL products; ALKALOIDS; TRYPTOPHAN; TROPINONES
- Publication
Chemical Record, 2019, Vol 19, Issue 2/3, p523
- ISSN
1527-8999
- Publication type
Article
- DOI
10.1002/tcr.201800079