170210-89-6Relevant articles and documents
Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels-Alder dimerisation
Comméiras, Laurent,Moses, John E.,Adlington, Robert M.,Baldwin, Jack E.,Cowley, Andrew R.,Baker, Christopher M.,Albrecht, Birgit,Grant, Guy H.
, p. 9892 - 9901 (2007/10/03)
An asymmetric total synthesis of the novel and structurally complex epoxyquinol natural product (+)-panepophenanthrin has been accomplished, in which a biomimetic Diels-Alder dimerisation is a key step. The key monomeric precursor was assembled by an effi
New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (-)-LL-C10037α, and (+)-KT 8110
Block, Oliver,Klein, Georg,Altenbach, Hans-Josef,Brauer, David J.
, p. 716 - 721 (2007/10/03)
A practical route is decribed for the preparation of the C7N core of manumycin-type compounds. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol. A diepoxy aminoinositol is accessible which can function for formation of enantiopure epoxyquinones and quinols. Examples are given for acylation reactions of this amine with several acyl derivatives. With this approach (-)-LL-C10037α and quinones such as (+)-KT-8110 with 5A,6S-configuration can be synthesized through oxidation. In addition a short route to (+)-bromoxone is described. Most steps include simple epoxide formation and cleavage reactions which all can be carried out in a high stereoselective manner.
De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation
Plettenburg,Adelt,Vogel,Altenbach
, p. 1057 - 1061 (2007/10/03)
The first total synthesis of Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4 is presented. Starting from p-benzoquinone, we took advantage of the C2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by s