27675-77-0Relevant academic research and scientific papers
Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones
Raffaelli, Barbara,Waehaelae, Kristiina,Hase, Tapio
, p. 331 - 341 (2008/01/27)
The asymmetric synthesis of a series of (7′S,8R,8′R)-7′- hydroxylignano-9,9′-lactones is presented, among them the mammalian lignan (7′S)-hydroxyenterolactone and (7′S)-parabenzlactone, allowing the stereochemistry of natural occurring (-)-parabenzlactone
Radical Cyclization in Heterocycle Synthesis. 11. A Novel Synthesis of α,β-Disubstituted γ-Lactones via Sulfanyl Radical Addition-Cyclization Using Hydroximates as a Tether
Miyata, Okiko,Nishiguchi, Atsuko,Ninomiya, Ichiya,Aoe, Keiichi,Okamura, Kimio,Naito, Takeaki
, p. 6922 - 6931 (2007/10/03)
A combination of sulfanyl radical addition-cyclization of dienes connected with hydroximates and subsequent conversion of the resulting cyclic hydroximate to the lactones provides a novel method for the construction of α,β-disubstituted γ-lactones. Upon treatment with thiophenol in the presence of AIBN, dienes connected with hydroximates smoothly underwent sulfanyl radical addition-cyclization to give cyclic cis- and trans-hydroximates. Hydrolysis of cyclic hydroximates gave the desired cis- and trans-lactones in high yield. This method was successfully applied to the practical synthesis of (±)-oxo-parabenzlactone.
Hydroximate as a synthetically useful functional group part II: Synthesis of (±)-oxo-parabenzlactone
Miyata, Okiko,Nishiguchi, Atsuko,Ninomiya, Ichiya,Naito, Takeaki
, p. 1285 - 1287 (2007/10/03)
A stereoselective route to (±)-oxo-parabenzlactone has been developed by the combination of thiyl radical addition-cyclization of dienylhydroximate and subsequent conversion of the resulting cyclic hydroximate to lactone.
