Total Syntheses of 2,2‘-epi-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin
- 14 March 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (13) , 4001-4013
- https://doi.org/10.1021/ja0685708
Abstract
The total syntheses of 2,2‘-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed “skyrane”. The strategies developed for their total synthesis feature a cascade sequence called the “cytoskyrin cascade” and deliver these molecules in short order and in a stereoselective manner.Keywords
This publication has 29 references indexed in Scilit:
- Bisanthraquinone Metabolites Produced by the Endophytic Fungus Diaporthe sp.CHEMICAL & PHARMACEUTICAL BULLETIN, 2006
- Simple, Efficient Chemoenzymatic Synthesis of (S)-5-(tert-Butyldimethylsilyloxy)-2-cyclohexenone and Enantiomeric Ketone Intermediates of 19-Nor-1α,25-dihydroxyvitamin D3The Journal of Organic Chemistry, 2001
- Reactions of N‐Methylenecarboxamides with Electrophiles: 1‐Alkoxy‐2‐azaallenium Salts and N‐Acyl(methylene)ammonium SaltsAngewandte Chemie International Edition in English, 1983
- The endiandric acid cascade. Electrocyclizations in organic synthesis. 4. Biomimetic approach to endiandric acids A-G. Total synthesis and thermal studiesJournal of the American Chemical Society, 1982
- The endiandric acid cascade. Electrocyclizations in organic synthesis. 2. Stepwise, stereocontrolled total synthesis of endiandric acids C-GJournal of the American Chemical Society, 1982
- Selective Photochemical Fries Rearrangement of Phenyl Acetate in the Presence of β‐CyclodextrinAngewandte Chemie International Edition in English, 1975
- Some recent studies on the metabolites of fungi and lichensPublished by Walter de Gruyter GmbH ,1973
- Correlation of some structural parameters of pyrimidine nucleosides. Nuclear magnetic resonance studyJournal of the American Chemical Society, 1971
- Bredt's rule. Bicyclo[3.3.1]non-1-eneJournal of the American Chemical Society, 1967
- Studies with the Amine Adducts of β-Benzoylacrylic Acid and its Methyl Ester1Journal of the American Chemical Society, 1956