The anti-Bredt red flag! Reassignment of neoveratrenone

Savchenko, Andrei I. and Williams, Craig M. (2013) The anti-Bredt red flag! Reassignment of neoveratrenone. European Journal of Organic Chemistry, Early View 32: 7263-7265. doi:10.1002/ejoc.201301308

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Author Savchenko, Andrei I.
Williams, Craig M.
Title The anti-Bredt red flag! Reassignment of neoveratrenone
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1434-193X
1099-0690
Publication date 2013-10
Year available 2013
Sub-type Article (original research)
DOI 10.1002/ejoc.201301308
Volume Early View
Issue 32
Start page 7263
End page 7265
Total pages 4
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag
Collection year 2014
Language eng
Formatted abstract
Over one hundred years ago, the German Professor Julius Bredt derived the “Bredtsche Regel” (Bredt's rule), which, in short, states that the terminus of a double bond cannot lie at a bridgehead position. The Bredt rule premise initiated the reassignment of the structure of the natural product neoveratrenone, which strongly suggested a C-nor-D-homo steroid as the correct structural assignment.

The bicyclo[3.3.1]non-1-en-3-one motif, which has yet to be observed in natural products, was recently reported within the skeleton of neoveratrenone. On the basis of Bredt's rule, a plausible reassignment matching closely the C-nor-D-homo steroidal ring system has been proposed herein.
Keyword Neoveratrenone
Steroids
Natural products
Structure elucidation
Bredt's rule
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 18 Oct 2013, 10:47:39 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences