1191083-30-3Relevant academic research and scientific papers
Assembly of a key dienic intermediate for tetrodotoxin via a Machetti-DeSarlo reaction
Chau, Jaclyn,Xu, Sanjia,Ciufolini, Marco A.
, p. 11901 - 11910 (2014/01/06)
A route to a racemic diene intermediate for the synthesis of tetrodotoxin is described. Key steps of the sequence leading to such a compound include the oxidative amidation of a phenol, a Cu(II)-catalyzed cyclocondensation of a nitroketone with an olefin (Machetti-DeSarlo reaction), and a nucleophilic fragmentation of the resulting isoxazoline. Several unusual reactions encountered in the course of this study are thoroughly discussed.
Synthetic aspects of the oxidative amidation of phenols
Liang, Huan,Ciufolini, Marco A.
scheme or table, p. 5884 - 5892 (2010/09/09)
The oxidative amidation of phenols effects the conversion of appropriately substituted phenols into 4-amidodienones ('para-oxidative amidation') or 2-amidodienones ('ortho-oxidative amidation') by the action of hypervalent iodine reagents. The reagent, (diacetoxyiodo)benzene ('DIB') is especially effective in these transformations. This paper focuses on techniques for the desymmetrization of the dienoes thus obtained, leading to the stereocontrolled creation of N-substituted spiro carbons. The methodology creates new opportunities in alkaloid synthesis, as apparent from a number of examples. DIB=PhI(OAc)2. The reaction may be carried out in the intra- or the intermolecular mode.
Approach to tetrodotoxin via the oxidative amidation of a phenol
Mendelsohn, Brian A.,Ciufolini, Marco A.
supporting information; experimental part, p. 4736 - 4739 (2009/12/24)
An approach to tetrodotoxin that relies on the oxidative amidation of methyl 4-hydroxyphenylacetate as a key step Is described. The stereoselective introduction of a β-hydroxynitrile functionality on one of the double bonds of the emerging dienone Is achi
