- Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels-Alder dimerisation
-
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
- 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)
-
- Flexible stereo- and regioselective synthesis of myo-inositol phosphates (part 1): Via symmetrical conduritol B derivatives
-
A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C2- symmetric diacetoxyconduritol B key in
- Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
-
p. 3101 - 3115
(2007/10/03)
-
- New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (-)-LL-C10037α, and (+)-KT 8110
-
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.
- Block, Oliver,Klein, Georg,Altenbach, Hans-Josef,Brauer, David J.
-
p. 716 - 721
(2007/10/03)
-
- A new resolution of (1α,2β,3α,4β)-2,3-dibromocyclohex-5-en-1,4-diol by lipase from Mucor miehei
-
An efficient resolution of 2,3-dibromocyclohex-5-en-1,4-diol has been carried out, using Mucor miehei lipase operating in an organic solvent. The enantioforms obtained may find application in the preparation of chiral conduritols. Copyright (C) 2000 Elsevier Science Ltd.
- Sanfilippo, Claudia,Patti, Angela,Nicolosi, Giovanni
-
p. 1043 - 1045
(2007/10/03)
-
- De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4-regiospecificity of their enzymatic dephosphorylation
-
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
- Plettenburg,Adelt,Vogel,Altenbach
-
p. 1057 - 1061
(2007/10/03)
-
- Enzyme-assisted total synthesis of the optical antipodes D-myo-inositol 3,4,5-trisphosphate and D-myo-inositol 1,5,6-trisphosphate: Aspects of their structure-activity relationship to biologically active inositol phosphates
-
Unambiguous total syntheses of both optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P3) and D- myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P3) are described. The ring system characteristic of
- Adelt, Stephan,Plettenburg, Oliver,Stricker, Rolf,Reiser, Georg,Altenbach, Hans-Josef,Vogel, Günter
-
p. 1262 - 1273
(2007/10/03)
-