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On the Rearrangement of an Azaspiroindolenine to a Precursor to Phalarine: Mechanistic Insights
Author(s) -
Li Chaomin,
Chan Collin,
Heimann Annekatrin C.,
Danishefsky Samuel J.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604071
Subject(s) - toluene , chemistry , sulfonyl , mechanism (biology) , ring (chemistry) , cope rearrangement , combinatorial chemistry , computer science , stereochemistry , organic chemistry , philosophy , epistemology , alkyl
An interesting rearrangement : Management of functional groups in derivatives of indoles enables a rearrangement to take place which provides the pentacyclic ring system found in phalarine (see scheme, CSA=camphorsulfonic acid, Ts=toluene‐4‐sulfonyl). Studies into the mechanism proved valuable for the total synthesis of phalarine and provided insight into the chemistry of indoles in general.