On the Rearrangement of an Azaspiroindolenine to a Precursor to Phalarine: Mechanistic Insights | Zendy

Li Chaomin | Zendy; Chan Collin | Zendy; Heimann Annekatrin C. | Zendy; Danishefsky Samuel J. | Zendy

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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.

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