Progress toward the total synthesis of (+)-aldosterone: synthesis of the A-D rings.
[reaction: see text] Synthesis of the A-D rings of the cortical hormone (+)-aldosterone is described. The key step incorporates a chiral tether in a type 2 intramolecular Diels-Alder reaction that establishes the absolute configuration of four contiguous asymmetric centers. This approach provides an efficient route for either enantiomer of the steroid skeleton.
Bear
Brian R
BR
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, Irvine, California 92697-2025, USA.
Parnes
Jason S
JS
Shea
Kenneth J
KJ
D000450:Aldosterone / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation
D007202:Indicators and Reagents; D000450:Aldosterone