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.
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, Irvine, California 92697-2025, USA.
Brian R
BR
Bear
Jason S
JS
Parnes
Kenneth J
KJ
Shea
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