Bear Brian R, Parnes Jason S, Shea Kenneth J
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, Irvine, California 92697-2025, USA.
Org Lett. 2003 May 15;5(10):1613-6. doi: 10.1021/ol034218c.
[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.