10.1039/P19810001603
The research focuses on the synthesis of perhydro-phenanthrene derivatives related to cheilanthatriol, a tricyclic sesterterpene. The primary purpose of the study was to achieve stereospecific syntheses of key intermediates, specifically 10a-hydroxy-1,1,4a,8a-tetramethyl-trans-transoid-trans-2,3,4,4a,4b,5,7,8,8a,9,10,10a-dodecahydrophenanthren-6(1H)-one (9) and 1,1,4a,8a-tetramethyl-8a-(3-methylpentanoyl)-2,3,4,4a,4b,5,7,8,8a,9-decahydrophenanthren-6(1H)-one (15). These compounds are potential intermediates in the synthesis of cheilanthatriol. The researchers used various chemical reactions and reagents, including Wolff-Kishner reduction, hydroboration, bromination, and conjugate addition, employing reagents such as lithium, liquid ammonia, sodium dichromate, and pyrrolidone hydrotribromide.