Unprecedented 1,14-seco-Crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer–Villiger rearrangement

Maslovskaya, Lidiya A., Savchenko, Andrei I., Pierce, Carly J., Gordon, Victoria A., Reddell, Paul W., Parsons, Peter G. and Williams, Craig M. (2014) Unprecedented 1,14-seco-Crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer–Villiger rearrangement. Chemistry: A European Journal, 20 44: 14226-14230. doi:10.1002/chem.201404250

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Author Maslovskaya, Lidiya A.
Savchenko, Andrei I.
Pierce, Carly J.
Gordon, Victoria A.
Reddell, Paul W.
Parsons, Peter G.
Williams, Craig M.
Title Unprecedented 1,14-seco-Crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer–Villiger rearrangement
Formatted title
Unprecedented 1,14-seco-Crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer–Villiger rearrangement
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 0947-6539
1521-3765
Publication date 2014-09-18
Year available 2014
Sub-type Article (original research)
DOI 10.1002/chem.201404250
Volume 20
Issue 44
Start page 14226
End page 14230
Total pages 5
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag
Collection year 2015
Language eng
Formatted abstract
EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C (4). Novel oxidative degradation products, EBC-233 and EBC-300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo-Baeyer–Villiger biosynthetic rearrangement to give a new class of 1,14-seco-crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 18 SEP 2014.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
School of Medicine Publications
 
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Created: Fri, 26 Sep 2014, 10:39:55 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences