193416-19-2Relevant academic research and scientific papers
Asymmetric Synthesis of (-)-Denticulatins A and B via Group-Selective Aldolization of a Meso Dialdehyde with a Chiral N-Propionylsultam.
Oppolzer, Wolfgang,Brabander, Jef De,Walther, Eric,Bernardinelli, Gerald
, p. 4413 - 4416 (1995)
Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is conve
Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step
De Brabander, Jef,Oppolzer, Wolfgang
, p. 9169 - 9202 (2007/10/03)
The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.
