Conformational locking through allylic strain as a device for stereocontrol - Total synthesis of grandisine A Journal Article

  


Authors: Maloney, D. J.; Danishefsky, S. J.
Article Title: Conformational locking through allylic strain as a device for stereocontrol - Total synthesis of grandisine A
Abstract: (Chemical Equation Presented) Controlled fusion: The use of a seco ring D precursor to control both the stereochemistry of a critical cycloaddition with acetaldehyde and the direction of protonation of the resultant silyl enol ether cycloadduct has led to the total synthesis of grandisine A, which shows promising selectivity for binding to the δ-opioid receptor. The D ring is installed in the final stages of the synthesis (see scheme, LA = Lewis acid). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords: unclassified drug; chemistry; binding energy; conformation; indolizines; aldehydes; molecular conformation; synthesis; total synthesis; stereochemistry; stereoisomerism; cycloaddition; natural products; ethers; allylic strain; steric hindrance; allylic strains; grandisines; silyl enol ethers; steric hindrances; protonation; grandisine a; indolizine derivative
Journal Title: Angewandte Chemie - International Edition
Volume: 46
Issue: 41
ISSN: 1433-7851
Publisher: Wiley Blackwell  
Date Published: 2007-10-15
Start Page: 7789
End Page: 7792
Language: English
DOI: 10.1002/anie.200703245
PUBMED: 17876796
PROVIDER: scopus
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-35349026226&partnerID=40&md5=2bb7d4cb5228ede25ced7b36414427f2
Notes: --- - "Cited By (since 1996): 4" - "Export Date: 17 November 2011" - "CODEN: ACIEA" - "Source: Scopus"
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MSK Authors
  1. David J Maloney
    2 Maloney
  2. Samuel J Danishefsky
    539 Danishefsky
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