ChemInform Abstract: FLUORINATED STEROIDS. I. 3‐FLUORO‐5,6‐UNSATURATED DERIVATIVES

Abstract

Umsetzung des Pregnenolons (I) mit dem Amin (II) in CHQCIQ, CHCl3, THF oder Acetonitril führt zu dem erwarteten Fluorid (IIIb) und den Derivaten (IIIa)‐(V), wobei die Produkt‐ Verteilung von dem eingesetzten Lösungsmittel abhängig ist (Bildungsmechanismen werden vorgeschlagen).

Dimeric and Oligomeric Steroids

“…Among other products consistent with the homoallylic intermediate 39 , the 3,3‘-ether of 3-hydroxypregn-5-en-20-one 40 was isolated from the reaction mixture of 3-hydroxypregn-5-en-20-one ( 36 ) and compound 37 (Scheme ) …”

“…Among other products consistent with the homoallylic intermediate 39, the 3,3′-ether of 3-hydroxypregn-5-en-20-one 40 was isolated from the reaction mixture of 3-hydroxypregn-5-en-20-one (36) and compound 37 (Scheme 11). 47 The structure of this dimeric steroid 40 was unambiguously established by NMR spectroscopy. The preparations of 3β,3β′-(methylenedioxy)dicholest-5-ene and 3β,3β′-(methylenedioxy)-5R,5R-dicholestane have been reported.…”

“…13 The same spacer group has been used to link two cholic acids together via the 17-side chain. Hoffmann and Kumpf 11 reported a synthesis whereby two estrones (47) are joined through the A-rings with terephthalic acid to give 48 (Scheme 13) and through the D-rings with p-phenylenediamine. The former (48) was capped with a para-substituted aniline and the latter with a para-substituted benzoic acid.…”

Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning

“…Homobenzylic alcohols 1z and 1aa (Figure D) afforded high yields, but may form via an arenium ion. The analogous competing homoallylic rearrangement resulted in low yield of 2ab . The α-hydroxycarbonyl compounds 1ac and 1ad performed reasonably well, but β-hydroxycarbonyl substrates afforded exclusively α,β-unsaturated products.…”