I came home and looked the tests up on the internet. I started reading everything that I could find. I knew then that I had Cushing’s. I found the Cushing’s help site. The trouble was that some tests were normal and some were abnormal. Finally in January of 2003 I went to see Dr. Friedman after another patient emailed me. Dr. Friedman tested my 17-Hydroxysteroids and 17- Ketosteroids which came back elevated. He also did some additional salivary cortisols testing. He finally figured out that I not only had Cyclic Cushing’s but also Acromegaly.
Allylic bromination (. with N-bromosuccinimide (NBS)) of 17β-acetoxyandrosta-1,4-dien-3-one 8 followed by treatment with zinc affords the non-conjugated enone 9. 1,4-Alkylation with lithiodimethyl cuprate provides the 1α-methyl ketone 10a. At this stage the 10a may be converted to a methylene by Wolff-Kishner reduction or the Huang Minlon modification thereof. These vigorous reaction conditions result in hydrolysis of the resulting carbon-17 acetate thereby yielding the hydroxy desoxy derivative, 17β-hydroxy-1α-methylandrost-5-ene (3b). Both 10a and its desoxy derivative can be converted via standard reactions, ., hydrolysis of the 17-acetate with sodium carbonate and methanol followed by chromium trioxide oxidation of the resulting 17-alcohol to the carbon-17 ketone. Selective reduction of the carbon-3 ketone, 3,17-diketone 3c using sodium borohydride pyridine (pyr) yields 1α-methyl dehydroepiandrosterone 3a.