Publications (2)6.82 Total impact
-
Article: Hyperconjugation involving strained carbon-carbon bonds. Application of the variable oxygen probe to ester and ether derivatives of cubylmethanol.
[show abstract] [hide abstract]
ABSTRACT: Application of the variable oxygen probe to derivatives of (4-methoxycarbonyl)cubylmethanol demonstrated a strong response of C-OR bond distance to the electron demand of the OR substituent, consistent with an enhanced σ-donor ability of the strained C-C bonds of cubane. The extent of cubane donor ability was found to be superior to an unstrained donor , comparing data extracted from the Cambridge Structural Database (T. W. Cole, Ph.D. Dissertation, University of Chicago, 1966), but weaker than the previously studied cyclopropane donors. Structural evidence is also found for σCC-π*CO interactions in these structures.Organic & Biomolecular Chemistry 03/2013; · 3.70 Impact Factor -
Article: Total synthesis of 2''',5'''-diepisilvestrol and its C1''' epimer: key structure activity relationships at C1''' and C2'''.
[show abstract] [hide abstract]
ABSTRACT: The first total synthesis of the low-abundance natural product 2''',5'''-diepisilvestrol (4) is described. The key step involved a Mitsunobu coupling between cyclopenta[b]benzofuran phenol 7 and dioxane lactol 6. Deprotection then gave a 1:2.6 ratio of natural product 2''',5'''-diepisilvestrol (4) and its C1 epimer 1''',2''',5'''-triepisilvestrol (15) in 50% overall yield. An in vitro protein translation inhibition assay showed that 2''',5'''-diepisilvestrol (4) was considerably less active than episilvestrol (2), while the unnatural isomer 1''',2''',5'''-triepisilvestrol (15) was essentially inactive, showing that the configuration at C1''' and C2''' has a large effect on the biological activity.Journal of Natural Products 07/2012; 75(8):1500-4. · 3.13 Impact Factor
Top co-authors
Top Journals
Institutions
-
2013
-
University of Melbourne
Melbourne, Victoria, Australia
-
