Journal
HETEROCYCLES
Volume 84, Issue 2, Pages 1325-1334Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-11-S(P)67
Keywords
Alkaloid; Indole; Dithioacetal; Sequential Reaction; Electrophilic Aromatic Substitution
Categories
Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- KAKENHI
- Cabinet Office, Government of Japan
- Astellas Foundation for Research on Metabolic Disorders
- [20390003]
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The common pentacyclic skeleton of indole diterpene alkaloids, paspaline and its derivatives was constructed by a sequential reaction. The appropriate choice of the protecting group on the indole nitrogen was critical for the formation of bis(methylthio)allylic alcohol, which then underwent sulfonium ion formation and intramolecular electrophilic C-C-bond formation at the indole 3-position.
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