On the rearrangement of an azaspiroindolenine to a precursor to phalarine: Mechanistic insights Journal Article

  


Authors: Li, C.; Chan, C.; Heimann, A. C.; Danishefsky, S. J.
Article Title: On the rearrangement of an azaspiroindolenine to a precursor to phalarine: Mechanistic insights
Abstract: (Chemical Equation Presented) 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. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords: chemistry; chemical structure; molecular structure; indoles; alkaloids; indole derivative; heterocyclic compound; models, chemical; synthesis (chemical); stereoisomerism; furan derivative; furans; derivatives; natural products; chemical model; organic compounds; alkaloid; rearrangement; aza compounds; retro-mannich reaction; sulfonation; crystalline materials
Journal Title: Angewandte Chemie - International Edition
Volume: 46
Issue: 9
ISSN: 1433-7851
Publisher: Wiley Blackwell  
Date Published: 2007-02-19
Start Page: 1444
End Page: 1447
Language: English
DOI: 10.1002/anie.200604071
PUBMED: 17387654
PROVIDER: scopus
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-34247851027&partnerID=40&md5=38c1aefba2d641a084b7efb83e17545a
Notes: --- - "Cited By (since 1996): 19" - "Export Date: 17 November 2011" - "CODEN: ACIEA" - "Source: Scopus"
Altmetric
What is Altmetric?
Citation Impact
What is Dimensions Citation Badge?
BMJ Impact Analytics
MSK Authors
  1. Annekatrin Charlotte Heimann
    3 Heimann
  2. Samuel J Danishefsky
    539 Danishefsky
Related MSK Work