169774-80-5Relevant articles and documents
Towards a versatile synthesis of kainoids III: Efficient methods for control of C-4 stereochemistry
Baldwin, Jack E.,Fryer, Andrew M.,Spyvee, Mark R.,Whitehead, Roger C.,Wood, Mark E.
, p. 5273 - 5290 (2007/10/03)
Halo- and selenolactonisation methods were used to prepare benzylic lactones from enamide carboxylic acids. The lactones were subsequently cleaved with predominantly inversion of configuration at the benzylic centre to give protected acromelic analogues with the correct C-4 stereochemistry. Hydroxyl directed heterogeneous hydrogenation of related enamide carbinols gave total stereocontrol at C-4.
Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry
Baldwin, Jack E.,Bamford, Samantha J.,Fryer, Andrew M.,Rudolph, Martin P. W.,Wood, Mark E.
, p. 5255 - 5272 (2007/10/03)
Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.
A versatile approach to acromelic acid analogues
Baldwin, Jack E.
, p. 4869 - 4872 (2007/10/02)
A route to acromelic acid analogues and their corresponding C-4 epimers from trans-4-hydroxy-L-proline is described. The C-4 substituent was introduced by a Suzuki-type boronate coupling to a vinyl triflate.
