153079-57-3Relevant academic research and scientific papers
Intramolecular vinyl quinone Diels-Alder reactions: Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol
Loebermann, Florian,Weisheit, Lara,Trauner, Dirk
, p. 4324 - 4326 (2013)
A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.
Redox-triggered C-c coupling of alcohols and vinyl epoxides: Diastereo- and enantioselective formation of all-carbon quaternary centers via tert -(Hydroxy)-prenylation
Feng, Jiajie,Garza, Victoria J.,Krische, Michael J.
, p. 8911 - 8914 (2014/07/08)
Iridium catalyzed primary alcohol oxidation triggers reductive C-O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin-Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations.
Epoxides from myrcene: Selective obention
Fauchet,Arreguy-San Miguel,Taran,Delmond
, p. 2503 - 2510 (2007/10/02)
1,2- and 3,10-epoxy myrcene are selectively obtained from dihydroxy derivatives prepared by an oxidation reaction of myrcene with potassium permanganate.
