81925-41-9Relevant academic research and scientific papers
A reductive cyclization approach to attenol A
La Cruz, Thomas E.,Rychnovsky, Scott D.
, p. 2602 - 2611 (2007/10/03)
A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.
Preparation and Reactions of Some Cyclic Orthoester Derivatives
Crich, David,Ritchie, Timothy J.
, p. 2319 - 2328 (2007/10/02)
Deprotonation of the alkoxysulphone (5) followed by quenching with diphenyl disulphide yields the dithioorthoester (6) and not the expected ketene monothioacetal (7).Attempts at orthoester exchange of (6) with decanol with a variety of reagents lead to ring opened products.Quenching of the anion derived from (5) with sulphuryl chloride or bromine leads respectively to the chloride (19) and bromide (20).Solvolysis of these halides leads to formation of sulphinate esters.
CYCLIC VINYL ETHER CARBANIONS-II PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL COMPOUNDS
Boeckman, Robert K.,Bruza, Kenneth J.
, p. 3997 - 4006 (2007/10/02)
Conditions for metalation of a variety of cyclic vinyl ethers and reaction of the resulting carbanions with electrophiles are described.Effects of the vinyl ether structure on the relative rates of metalation are discussed.Applications of this methodology
